2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides

ABSTRACT

The invention relates to novel compounds of the formula (I) 
                         
in which the R 1 , R 2a , R 2b , R 3 , A 1 , A 2 , A 4  and n have the meanings given above, to their use as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for their preparation.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a § 371 National State Application ofPCT/EP2016/052105, filed Feb. 2, 2016, which claims priority to EuropeanApplication Nos. 15153948.3 filed Feb. 5, 2015 and 15171696.6 filed Jun.11, 2015.

BACKGROUND Field of the Invention

The present invention relates to novel 2-(het)aryl-substituted fusedbicyclic heterocycle derivatives of the formula (I), to the use thereofas acaricides and/or insecticides for controlling animal pests,particularly arthropods and especially insects and arachnids, and toprocesses and intermediates for preparation thereof.

Description of Related Art

2-(Het)aryl-substituted fused bicyclic heterocycle derivatives havinginsecticidal properties have already been described in the literature,for example in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO2013/018928, WO 2014/142292 and WO 2014/148451, and also WO 2015/000715,WO 2015/121136 and WO 2015/002211.

However, the active compounds already known according to the documentscited above have some disadvantages on application, whether because theyexhibit only a narrow range of application or because they do not havesatisfactory insecticidal or acaricidal activity.

SUMMARY

Novel 2-(het)aryl-substituted fused bicyclic heterocycle derivativeshave now been found, and these have advantages over the compoundsalready known, examples of which are better biological or environmentalproperties, a wider range of application methods, better insecticidal oracaricidal activity, and also good compatibility with crop plants. The2-(het)aryl-substituted fused bicyclic heterocycle derivatives can beused in combination with further agents for improving efficacy,especially against insects that are difficult to control.

The present invention therefore provides novel compounds of the formula(I)

-   in which (configuration 1)-   A¹ represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² represents —N—R⁵, oxygen or sulphur,-   A⁴ represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   R¹ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)cycloalkyl, amino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, (C₃-C₈)-cycloalkylamino,    (C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphonylamino, aminosulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylaminosulphonyl-(C₁-C₆)-alkyl,    di-(C₁-C₆)-alkylaminosulphonyl-(C₁-C₆)-alkyl,    -   or represents (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, each of which is optionally        mono- or polysubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl and heterocyclyl may each optionally be        mono- or polysubstituted by identical or different substituents        from the group consisting of halogen, cyano, nitro, hydroxy,        amino, carboxy, carbamoyl, aminosulphonyl, (C₁-C₆)-alkyl,        (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,        (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-alkylsulphimino,        (C₁-C₆)-alkylsulphimino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulphimino-(C₂-C₆)-alkylcarbonyl,        (C₁-C₆)-alkylsulphoximino,        (C₁-C₆)-alkylsulphoximino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulphoximino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,        (C₃-C₆)-trialkylsilyl and benzyl, or-   R¹ represents aryl, hetaryl or heterocyclyl, each of which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, cyano, nitro,    hydroxy, amino, carboxy, carbamoyl, (C₁-C₆)-alkyl,    (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-alkylsulphimino,    (C₁-C₆)-alkylsulphimino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphimino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylsulphoximino, (C₁-C₆)-alkylsulphoximino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphoximino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₆)-trialkylsilyl, (═O) (only in the case of heterocyclyl) and    (═O)₂ (only in the case of heterocyclyl),-   R^(2a), R³ and R⁴ independently of one another represent hydrogen,    cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,    tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)cycloalkyl, halo-(C₃-C₈)cycloalkyl,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyl,    (C₁-C₆)-haloalkylsulphonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl,    (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,    (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulphonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulphonyl,    (C₁-C₆)-alkylaminosulphonyl, di-(C₁-C₆)-alkylaminosulphonyl,    (C₁-C₆)-alkylsulphoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino),    -   represent aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, carboxyl, halogen, nitro, acetyl,        hydroxy, amino, SCN, tri-(C₁-C₆)-alkylsilyl, (C₁-C₆)-alkyl,        (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,        (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl(C₁-C₆)-alkoxyimino,        (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,        (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphinyl,        (C₁-C₆)-haloalkylsulphinyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl,        (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₆)-haloalkylsulphonyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl,        (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyloxy,        (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,        (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,        (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,        (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulphonylamino,        (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulphonyl,        (C₁-C₆)-alkylaminosulphonyl, di-(C₁-C₆)-alkylaminosulphonyl,        (C₁-C₆)-alkylsulphoximino, aminothiocarbonyl,        (C₁-C₆)-alkylaminothiocarbonyl,        di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,-   R^(2b) represents a group selected from —C(═O)—R⁸ (Q1), —C(═S)—R⁸    (Q2), —C(═O)—NR¹¹R¹² (Q3), —C(═S)—NR¹¹R¹² (Q4), —S(O)_(m)—R¹³ (Q5),    —S═O(═NH)—R³ (Q6), —S═O(═N—CN)—R³ (Q7), —S(═N—CN)—R¹³ (Q8),    —S(O)₂—NR¹¹R¹² (Q9), —NR¹¹R¹² (Q10), —NR¹¹—NR¹¹R¹² (Q11),    —NR¹¹—C(═O)—R⁸ (Q12), —NR¹¹—C(═S)—R⁸ (Q13), —NR¹¹—S(O)₂—R¹³ (Q14),    —N(R¹¹)—O—R¹³ (Q15), —N═S(═O)_(p)—R¹⁴R¹⁵ (Q16) and —O—R¹³ (Q17),    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent (C₁-C₆)-alkyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent        (C₁-C₆)-alkyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R⁵ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)cycloalkyl,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    aminocarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylamino-(C₁-C₆)-alkyl,    di-(C₁-C₆)-alkylamino-(C₁-C₆)-alkyl or    (C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl,-   R⁸ represents hydrogen or represents C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₃-C₁₂-cycloalkyl,    C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or C₄-C₁₂-bicycloalkyl, each of which    is optionally mono- or polysubstituted by identical or different    substituents, where the substituents independently of one another    may be selected from the group consisting of halogen, cyano, nitro,    hydroxy, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,    C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,    C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,    C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,    C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,    di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring and a 3-    to 6-membered aromatic, partially saturated or saturated    heterocycle, where the phenyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,    CN, (C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,    C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,    (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₄-alkyl)aminocarbonyl, tri-(C₁-C₂)-alkylsilyl,    (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or-   R⁸ represents a phenyl ring or a 3- to 6-membered aromatic,    partially saturated or saturated heterocycle, where the heteroatoms    are selected from the group consisting of N, S and O, where the    phenyl ring or heterocycle may in each case optionally be mono- or    polysubstituted by identical or different substituents, and where    the substituents independently of one another may be selected from    the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,    C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH,    CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,    C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,    (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,    (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    tri-(C₁-C₂)-alkylsilyl, (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another represent    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₁₂-cycloalkyl,    C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or C₄-C₁₂-bicycloalkyl, each of which    is optionally mono- or polysubstituted by identical or different    substituents, where the substituents independently of one another    may be selected from the group consisting of halogen, cyano, nitro,    hydroxy, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,    C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,    C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,    C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,    C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,    di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3-    or 6-membered aromatic, partially saturated or saturated    heterocycle, where the phenyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,    cyano, (C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,    C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,    (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₄-alkyl)aminocarbonyl, tri-(C₁-C₂)-alkylsilyl,    (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another represent a phenyl    ring or a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle, where the heteroatoms are selected from the    group consisting of N, S and O, where the phenyl ring or heterocycle    may in each case optionally be mono- or polysubstituted by identical    or different substituents, and where the substituents independently    of one another may be selected from the group consisting of    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,    C₃-C₆-halocycloalkyl, halogen, cyano, (C═O)OH, CONH₂, NO₂, OH,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,    C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,    (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,    (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    tri-(C₁-C₂)-alkylsilyl, (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,-   R¹¹, R¹² independently of one another represent hydrogen or    represent R⁹,-   m represents 0, 1 or 2,-   n represents 0, 1 or 2,-   p represents 0 or 1.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

It has additionally been found that the compounds of the formula (I)have very good efficacy as pesticides, preferably as insecticides and/oracaricides, and additionally generally have very good plantcompatibility, in particular with respect to crop plants.

A general definition of the compounds of the invention is provided bythe formula (I). Preferred substituents or ranges of the radicals givenin the formulae mentioned above and below are illustrated hereinafter:

Configuration 1-1:

-   R¹, R^(2a), R^(2b), R³, R⁴, R⁵, R⁸, R¹¹, R¹², A¹, A², A⁴, m, n and p    have the meanings given for Configuration 1 and R⁹, R¹³, R¹⁴, R¹⁵    independently of one another represent C₁-C₆-alkylsulphonyl or    represent C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₁₂-cycloalkyl, C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or    C₄-C₁₂-bicycloalkyl, each of which is optionally mono- or    polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from the    group consisting of halogen, cyano, nitro, hydroxy, C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,    C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,    C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,    C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,    di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3-    or 6-membered aromatic, partially saturated or saturated    heterocycle, where the phenyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,    cyano, (C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,    C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,    (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₄-alkyl)aminocarbonyl, tri-(C₁-C₂)-alkylsilyl,    (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another represent a phenyl    ring or a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle, where the heteroatoms are selected from the    group consisting of N, S and O, where the phenyl ring or heterocycle    may in each case optionally be mono- or polysubstituted by identical    or different substituents, and where the substituents independently    of one another may be selected from the group consisting of    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,    C₃-C₆-halocycloalkyl, halogen, cyano, (C═O)OH, CONH₂, NO₂, OH,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,    C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,    (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,    (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    tri-(C₁-C₂)-alkylsilyl, (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,    Configuration 1-2:-   A¹ represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² represents —N—R⁵, oxygen or sulphur,-   A⁴ represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   R¹ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)cycloalkyl, amino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, (C₃-C₈)-cycloalkylamino,    (C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphonylamino, aminosulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylaminosulphonyl-(C₁-C₆)-alkyl,    di-(C₁-C₆)-alkylaminosulphonyl-(C₁-C₆)-alkyl,    -   or represents (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, each of which is optionally        mono- or polysubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl and heterocyclyl may each optionally be        mono- or polysubstituted by identical or different substituents        from the group consisting of halogen, cyano, nitro, hydroxy,        amino, carboxy, carbamoyl, aminosulphonyl, (C₁-C₆)-alkyl,        (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,        (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-alkylsulphimino,        (C₁-C₆)-alkylsulphimino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulphimino-(C₂-C₆)-alkylcarbonyl,        (C₁-C₆)-alkylsulphoximino,        (C₁-C₆)-alkylsulphoximino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulphoximino-(C₂-C₆)alkylcarbonyl,        (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,        (C₃-C₆)-trialkylsilyl and benzyl, or-   R¹ represents aryl, hetaryl or heterocyclyl, each of which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, cyano, nitro,    hydroxy, amino, carboxy, carbamoyl, (C₁-C₆)-alkyl,    (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-alkylsulphimino,    (C₁-C₆)-alkylsulphimino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphimino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylsulphoximino, (C₁-C₆)-alkylsulphoximino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphoximino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₆)-trialkylsilyl, (═O) (only in the case of heterocyclyl) and    (═O)₂ (only in the case of heterocyclyl),-   R^(2a), R³ and R⁴ independently of one another represent hydrogen,    cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,    tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)cycloalkyl, halo-(C₃-C₈)cycloalkyl,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkinyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl,    (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyl,    (C₁-C₆)-haloalkylsulphonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl,    (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,    (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulphonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulphonyl,    (C₁-C₆)-alkylaminosulphonyl, di-(C₁-C₆)-alkylaminosulphonyl,    (C₁-C₆)-alkylsulphoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino),    -   represent aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, carboxyl, halogen, nitro, acetyl,        hydroxy, amino, SCN, tri-(C₁-C₆)-alkylsilyl, (C₁-C₆)-alkyl,        (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,        (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,        (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,        (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphinyl,        (C₁-C₆)-haloalkylsulphinyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl,        (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₆)-haloalkylsulphonyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl,        (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulphonyloxy,        (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,        (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,        (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,        (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulphonylamino,        (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulphonyl,        (C₁-C₆)-alkylaminosulphonyl, di-(C₁-C₆)-alkylaminosulphonyl,        (C₁-C₆)-alkylsulphoximino, aminothiocarbonyl,        (C₁-C₆)-alkylaminothiocarbonyl,        di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,-   R^(2b) represents a group selected from —C(═O)—R⁸ (Q1), —C(═S)—R⁸    (Q2), —C(═O)—NR¹¹R¹² (Q3), —C(═S)—NR¹¹R¹² (Q4), —S(O)_(m)—R¹³ (Q5),    —S═O(═NH)—R³ (Q6), —S═O(═N—CN)—R³ (Q7), —S(═N—CN)—R¹³ (Q8),    —S(O)₂—NR¹¹R¹² (Q9), —NR¹¹R¹² (Q10), —NR¹¹—NR¹¹R¹² (Q11),    —NR¹¹—C(═O)—R⁸ (Q12), —NR¹¹—C(═S)—R⁸ (Q13), —NR¹¹—S(O)₂—R¹³ (Q14),    —N(R¹¹)—O—R¹³ (Q15), —N═S(═O)_(p)—R¹⁴R¹⁵ (Q16), —O—R¹³ (Q17) or    —C¹¹═CR⁸R¹² (Q18),    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent (C₁-C₆)-alkyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent        (C₁-C₆)-alkyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R⁵ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)cycloalkyl,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulphonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    aminocarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylamino-(C₁-C₆)-alkyl,    di-(C₁-C₆)-alkylamino-(C₁-C₆)-alkyl or    (C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl,-   R⁸ represents hydrogen or represents C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₃-C₁₂-cycloalkyl,    C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or C₄-C₁₂-bicycloalkyl, each of which    is optionally mono- or polysubstituted by identical or different    substituents, where the substituents independently of one another    may be selected from the group consisting of halogen, cyano, nitro,    hydroxy, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,    C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,    C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,    C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,    C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,    di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring and a 3-    to 6-membered aromatic, partially saturated or saturated    heterocycle, where the phenyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,    CN, (C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,    C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,    (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₄-alkyl)aminocarbonyl, tri-(C₁-C₂)-alkylsilyl,    (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or-   R⁸ represents a phenyl ring, a benzyl ring or a 3- to 6-membered    aromatic, partially saturated or saturated heterocycle, where the    heteroatoms are selected from the group consisting of N, S and O,    where the phenyl ring or the benzyl ring or heterocycle may in each    case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,    C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, CONH₂, NO₂, OH,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,    C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,    (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,    (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    tri-(C₁-C₂)-alkylsilyl, (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another represent    C₁-C₆-alkylsulphonyl or represent C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₁₂-cycloalkyl, C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or    C₄-C₁₂-bicycloalkyl, each of which is optionally mono- or    polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from the    group consisting of halogen, cyano, nitro, hydroxy, C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,    C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,    C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,    C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,    C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,    di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3-    to 6-membered aromatic, partially saturated or saturated    heterocycle, where the phenyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,    cyano, (C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,    C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,    (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₄-alkyl)aminocarbonyl, tri-(C₁-C₂)-alkylsilyl,    (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another represent a phenyl    ring, a benzyl ring or a 3- to 6-membered aromatic, partially    saturated or saturated heterocycle, where the heteroatoms are    selected from the group consisting of N, S and O, where the phenyl    ring, the benzyl ring or heterocycle may in each case optionally be    mono- or polysubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,    C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, cyano, (C═O)OH,    CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,    C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,    (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,    (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    tri-(C₁-C₂)-alkylsilyl, (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,-   R¹¹, R¹² independently of one another represent hydrogen or    represent R⁹,-   m represents 0, 1 or 2,-   n represents 0, 1 or 2,-   p represents 0 or 1.    Configuration 2:-   A¹ preferably represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² preferably represents —N—R⁵, oxygen or sulphur,-   A⁴ preferably represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   R¹ preferably represents (C₁-C₄)-alkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₂-C₄)-cyanoalkynyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino,    (C₁-C₄)-alkylcarbonylamino, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylcarbonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonylamino,    -   or represents (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl, (C₃-C₆)cycloalkyl, each of which is optionally        mono- or disubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl and heterocyclyl may in each case optionally        be mono- or disubstituted by identical or different substituents        from the group consisting of halogen, cyano, carbamoyl,        aminosulphonyl, (C₁-C₄)-alkyl, (C₃-C₄)-cycloalkyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkylsulphimino, or-   R¹ preferably represents aryl, hetaryl or heterocyclyl, each of    which is optionally mono- or disubstituted by identical or different    substituents from the group consisting of halogen, cyano, carbamoyl,    (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-alkylsulphimino, (C₁-C₄)-alkylsulphoximino,    (C₁-C₄)-alkylcarbonyl, (C₃-C₄)-trialkylsilyl, (═O) (only in the case    of heterocyclyl) and (═O)₂ (only in the case of heterocyclyl),-   R^(2a), R³ and R⁴ independently of one another preferably represent    hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,    tri-(C₁-C₄)-alkylsilyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,    (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,    (C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-haloalkylsulphinyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyloxy, (C₁-C₄)-alkylcarbonyl,    (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    (C₁-C₄)-alkylsulphonylamino, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, aminosulphonyl, (C₁-C₄)-alkylaminosulphonyl,    di-(C₁-C₄)-alkylaminosulphonyl, aminothiocarbonyl,    NHCO—(C₁-C₄)-alkyl ((C₁-C₄)-alkylcarbonylamino), or    -   represent phenyl or hetaryl, each of which is optionally mono-        or disubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, halogen, nitro, acetyl, amino,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,        (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl,        (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,        (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,        (C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,        (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,        (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-haloalkylsulphinyl,        (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphonyl,        (C₁-C₄)-haloalkylsulphonyl,        (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphonyloxy,        (C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,        (C₁-C₄)-alkylsulphonylamino, (C₁-C₄)-alkylamino,        di-(C₁-C₄)-alkylamino, aminosulphonyl,        (C₁-C₄)-alkylaminosulphonyl, di-(C₁-C₄)-alkylaminosulphonyl,-   R^(2b) preferably represents a group selected from Q1, Q2, Q3, Q4,    Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15, Q16, Q17 and Q18,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent        (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R⁵ preferably represents (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,-   R⁸ preferably represents hydrogen, represents C₁-C₄-alkyl,    C₃-C₆-cycloalkyl or C₁-C₄-alkoxy, each of which is optionally mono-    or polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from the    group consisting of halogen, cyano, a phenyl ring and a 3- to    6-membered aromatic, partially saturated or saturated heterocycle,    where the phenyl ring or heterocycle may in each case optionally be    mono- or polysubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,    cyano, NO₂, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,-   R⁸ preferably represents a phenyl ring or a 3- to 6-membered    aromatic, partially saturated or saturated heterocycle, where the    heteroatoms are selected from the group consisting of N, S and O,    where the phenyl ring or heterocycle may in each case optionally be    mono- or polysubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen    and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another preferably represent    C₁-C₄-alkyl or C₃-C₆-cycloalkyl, each of which is optionally mono-    or polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from the    group consisting of halogen, cyano, a phenyl ring and a 3- to    6-membered aromatic, partially saturated or saturated heterocycle,    where the phenyl ring or heterocycle may in each case optionally be    mono- or polysubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,    cyano, NO₂, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another preferably represent    a phenyl ring or a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle, where the heteroatoms are selected from the    group consisting of N, S and O, where the phenyl ring or heterocycle    may in each case optionally be mono- or polysubstituted by identical    or different substituents, and where the substituents independently    of one another may be selected from the group consisting of    C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano,-   R¹¹, R¹² independently of one another preferably represent hydrogen    or represent R⁹,-   m preferably represents 0, 1 or 2,-   n preferably represents 0, 1 or 2,-   p preferably represents 0 or 1.    Configuration 2-1:-   R¹, R^(2a), R^(2b), R³, R⁴, R⁵, R¹¹, R¹², A¹, A², A⁴, m, n and p    have the meanings given for Configuration 1 and-   R⁸ preferably represents hydrogen, represents C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl or C₁-C₄-alkoxy, each    of which is optionally mono- or polysubstituted by identical or    different substituents, where the substituents independently of one    another may be selected from the group consisting of halogen, cyano,    a phenyl ring and a 3- to 6-membered aromatic, partially saturated    or saturated heterocycle, where the phenyl ring or heterocycle may    in each case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy and    C₁-C₄-haloalkoxy,-   R⁸ preferably represents a phenyl ring or a 3- to 6-membered    aromatic, partially saturated or saturated heterocycle, where the    heteroatoms are selected from the group consisting of N, S and O,    where the phenyl ring or heterocycle may in each case optionally be    mono- or polysubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen    and cyano,-   R⁹, R¹³, R¹⁴, R⁵ independently of one another preferably represent    C₁-C₄-alkylsulphonyl, represent C₁-C₄-alkyl or C₃-C₆-cycloalkyl,    each of which is optionally mono- or polysubstituted by identical or    different substituents, where the substituents independently of one    another may be selected from the group consisting of halogen, cyano,    a phenyl ring and a 3- to 6-membered aromatic, partially saturated    or saturated heterocycle, where the phenyl ring or heterocycle may    in each case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy and    C₁-C₄-haloalkoxy,-   R⁹, R¹³, R¹⁴, R⁵ independently of one another preferably represent a    phenyl ring or a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle, where the heteroatoms are selected from the    group consisting of N, S and O, where the phenyl ring or heterocycle    may in each case optionally be mono- or polysubstituted by identical    or different substituents, and where the substituents independently    of one another may be selected from the group consisting of    C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano.    Configuration 2-2:-   A¹ preferably represents nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   A² preferably represents —N—R⁵, oxygen or sulphur,-   A⁴ is preferably nitrogen, ═N⁺—O⁻ or ═C—R⁴,-   R¹ preferably represents (C₁-C₄)-alkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₂-C₄)-cyanoalkynyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino,    (C₁-C₄)-alkylcarbonylamino, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylcarbonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonylamino, or represents (C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₃-C₆)cycloalkyl,    each of which is optionally mono- or disubstituted by identical or    different substituents from the group consisting of aryl, hetaryl    and heterocyclyl, where aryl, hetaryl and heterocyclyl may in each    case optionally be mono- or disubstituted by identical or different    substituents from the group consisting of halogen, cyano, carbamoyl,    aminosulphonyl, (C₁-C₄)-alkyl, (C₃-C₄)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-alkylsulphimino, or-   R¹ preferably represents aryl, hetaryl or heterocyclyl, each of    which is optionally mono- or disubstituted by identical or different    substituents from the group consisting of halogen, cyano, carbamoyl,    (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-alkylsulphimino, (C₁-C₄)-alkylsulphoximino,    (C₁-C₄)-alkylcarbonyl, (C₃-C₄)-trialkylsilyl, (═O) (only in the case    of heterocyclyl) and (═O)₂ (only in the case of heterocyclyl),-   R^(2a), R³ and R⁴ independently of one another preferably represent    hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,    tri-(C₁-C₄)-alkylsilyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,    (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,    (C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-haloalkylsulphinyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyloxy, (C₁-C₄)-alkylcarbonyl,    (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl,    (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    (C₁-C₄)-alkylsulphonylamino, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, aminosulphonyl, (C₁-C₄)-alkylaminosulphonyl,    di-(C₁-C₄)-alkylaminosulphonyl, aminothiocarbonyl,    NHCO—(C₁-C₄)-alkyl ((C₁-C₄)-alkylcarbonylamino), or    -   represent phenyl or hetaryl, each of which is optionally mono-        or disubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, halogen, nitro, acetyl, amino,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,        (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl,        (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,        (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,        (C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,        (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,        (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-haloalkylsulphinyl,        (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphonyl,        (C₁-C₄)-haloalkylsulphonyl,        (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulphonyloxy,        (C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,        (C₁-C₄)-alkylsulphonylamino, (C₁-C₄)-alkylamino,        di-(C₁-C₄)-alkylamino, aminosulphonyl,        (C₁-C₄)-alkylaminosulphonyl, di-(C₁-C₄)-alkylaminosulphonyl,-   R^(2b) preferably represents a group selected from Q1, Q2, Q3, Q4,    Q5, Q6, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15, Q16, Q17 and Q18,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent        (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q5, Q6, Q8 or Q9, n represents 2,-   R⁵ preferably represents (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulphonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,-   R⁸ preferably represents hydrogen, represents C₁-C₄-alkyl,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy or    C₁-C₄-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- or    polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from    halogen, cyano, a phenyl ring or a 3- to 6-membered aromatic,    partially saturated or saturated heterocycle, where the phenyl ring    or heterocycle may in each case optionally be mono- or    polysubstituted by identical or different substituents, and where    the substituents independently of one another may be selected from    the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,    cyano, NO₂, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,-   R⁸ preferably represents a phenyl ring, a benzyl ring or a 3- to    6-membered aromatic, partially saturated or saturated heterocycle,    where the heteroatoms are selected from the group consisting of N, S    and O, where the phenyl ring or the benzyl ring or heterocycle may    in each case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another preferably represent    C₁-C₄-alkylsulphonyl, represent C₁-C₄-alkyl or C₃-C₆-cycloalkyl,    each of which is optionally mono- or polysubstituted by identical or    different substituents, where the substituents independently of one    another may be selected from the group consisting of halogen, cyano,    a phenyl ring and a 3- to 6-membered aromatic, partially saturated    or saturated heterocycle, where the phenyl ring or heterocycle may    in each case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy and    C₁-C₄-haloalkoxy,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another preferably represent    a phenyl ring, a benzyl ring or a 3- to 6-membered aromatic,    partially saturated or saturated heterocycle, where the heteroatoms    are selected from the group consisting of N, S and O, where the    phenyl ring or the benzyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, halogen and cyano,-   R¹¹, R¹² independently of one another preferably represent hydrogen    or represent R⁹,-   m preferably represents 0, 1 or 2,-   n preferably represents 0, 1 or 2,-   p preferably represents 0 or 1.    Configuration 3:-   A¹ particularly preferably represents nitrogen or ═C—R⁴,-   A² particularly preferably represents —N—R⁵ or oxygen,-   A⁴ particularly preferably represents ═C—H,-   R¹ particularly preferably represents (C₁-C₄)-alkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl,-   R^(2a) particularly preferably represents hydrogen, cyano,    aminocarbonyl, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulphinyl or (C₁-C₄)-haloalkylsulphonyl,-   R^(2b) particularly preferably represents a group selected from Q1,    Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15, Q16    and Q17,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent methyl, ethyl, isopropyl, tert-butyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent methyl,        ethyl, isopropyl, tert-butyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R³ particularly preferably represents hydrogen, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl or    (C₁-C₄)-haloalkylsulphonyl,-   R⁴ particularly preferably represents hydrogen, halogen, cyano or    (C₁-C₄)-alkyl,-   R⁵ particularly preferably represents (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   R⁸ particularly preferably represents hydrogen, represents methyl,    ethyl, isopropyl, tert-butyl, methoxy or ethoxy, each of which is    optionally monosubstituted by halogen, cyano, phenyl or pyridyl,    where phenyl and pyridyl may each be mono- or disubstituted by    identical or different substituents from the group consisting of    trifluoromethyl, cyano, fluorine, chlorine, bromine and    trifluoromethoxy, or-   R⁸ particularly preferably represents phenyl, pyridyl or a 3- to    6-membered saturated heterocycle comprising 1-2 heteroatoms from the    group consisting of N, S and O, where phenyl, pyridyl and the    heterocycle may each optionally be mono- or disubstituted by    identical or different substituents, and where the substituents    independently of one another may be selected from C₁-C₄-alkyl,    C₁-C₄-haloalkyl, halogen and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another particularly    preferably represent methyl, ethyl, isopropyl or tert-butyl, each of    which may optionally be monosubstituted by halogen, cyano, phenyl or    pyridyl, where phenyl and pyridyl may each optionally be mono- or    disubstituted by identical or different substituents from the group    consisting of trifluoromethyl, cyano, fluorine, chlorine and    trifluoromethoxy, or-   R⁹, R¹³, R¹⁴, R⁵ independently of one another particularly    preferably represent phenyl, pyridyl or a 3- to 6-membered saturated    heterocycle comprising 1-2 heteroatoms from the group consisting of    N, S and O, where phenyl, pyridyl and the heterocycle may each be    mono- or disubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen    and cyano,-   R¹, R¹² independently of one another particularly preferably    represent hydrogen or represent R⁹,-   m particularly preferably represents 0, 1 or 2,-   n particularly preferably represents 0, 1 or 2,-   p particularly preferably represents 0 and 1.    Configuration 3-1:-   A¹ particularly preferably represents nitrogen or ═C—R⁴,-   A² particularly preferably represents —N—R⁵ or oxygen,-   A⁴ particularly preferably represents ═C—H,-   R¹ particularly preferably represents (C₁-C₄)-alkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl or benzyl,-   R^(2a) particularly preferably represents hydrogen, cyano,    aminocarbonyl, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulphinyl or (C₁-C₄)-haloalkylsulphonyl,-   R^(2b) particularly preferably represents a group selected from Q1,    Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15, Q16    and Q17,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q17, R³ does not represent        (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R³ particularly preferably represents hydrogen, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl or    (C₁-C₄)-haloalkylsulphonyl,-   R⁴ particularly preferably represents hydrogen, halogen, cyano or    (C₁-C₄)-alkyl,-   R⁵ particularly preferably represents (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   R⁸ particularly preferably represents hydrogen, represents    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxyalkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy, or-   R⁸ particularly preferably represents phenyl, pyridyl or pyrazolyl,    where phenyl, pyridyl and pyrazolyl may in each case optionally be    mono- or disubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen    and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another particularly    preferably represent (C₁-C₄)-alkyl, benzyl or    (C₁-C₄)-alkylsulphonyl, or-   R⁹, R¹³, R¹⁴, R⁵ independently of one another particularly    preferably represent phenyl, pyridyl or pyrazolyl, where phenyl,    pyridyl and pyrazolyl may in each case optionally be mono- or    disubstituted by identical or different substituents, and where the    substituents independently of one another may be selected from the    group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano,-   R¹¹, R¹² independently of one another particularly preferably    represent hydrogen or represent R⁹,-   m particularly preferably represents 0, 1 or 2,-   n particularly preferably represents 0, 1 or 2,-   p particularly preferably represents 0 and 1.    Configuration 3-2:-   A¹ particularly preferably represents nitrogen or ═C—R⁴,-   A² particularly preferably represents —N—R⁵ or oxygen,-   A⁴ particularly preferably represents ═C—H,-   R¹ particularly preferably represents (C₁-C₄)-alkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl or benzyl,-   R^(2a) particularly preferably represents hydrogen, cyano,    aminocarbonyl, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulphinyl or (C₁-C₄)-haloalkylsulphonyl,-   R^(2b) particularly preferably represents a group selected from Q1,    Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q17 and Q18,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q17, R³ does not represent        (C₁-C₄)-alkyl,    -   where, if R^(2b) represents Q5, Q6, Q8 or Q9, n represents 2,-   R³ particularly preferably represents hydrogen, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl or    (C₁-C₄)-haloalkylsulphonyl,-   R⁴ particularly preferably represents hydrogen, halogen, cyano or    (C₁-C₄)-alkyl,-   R⁵ particularly preferably represents (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   R⁸ particularly preferably represents hydrogen, represents    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₄)-alkylsulphinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulphonyl-(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl or (C₁-C₄)-alkoxy, or-   R⁸ particularly preferably represents phenyl, benzyl, pyridyl,    thiazolyl or pyrazolyl, where phenyl, benzyl, pyridyl, thiazolyl and    pyrazolyl may in each case optionally be mono- or disubstituted by    identical or different substituents, and where the substituents    independently of one another may be selected from the group    consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another particularly    preferably represent (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, acetyl,    (C₃-C₆)-cycloalkyl, benzyl or (C₁-C₄)-alkylsulphonyl, or-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another particularly    preferably represent phenyl, pyridyl or pyrazolyl, where phenyl,    pyridyl and pyrazolyl may in each case optionally be mono- or    disubstituted by identical or different substituents, and where the    substituents independently of one another may be selected from the    group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano,-   R¹¹, R¹² independently of one another particularly preferably    represent hydrogen or represent R⁹,-   m particularly preferably represents 0, 1 or 2,-   n particularly preferably represents 0, 1 or 2.    Configuration 4:-   A¹ very particularly preferably represents nitrogen or ═C—R⁴,-   A² very particularly preferably represents —N—R⁵ or oxygen,-   A⁴ very particularly preferably represents ═C—H,-   R¹ very particularly preferably represents methyl, ethyl, n-propyl,    isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R^(2a) very particularly preferably represents hydrogen, cyano,    aminocarbonyl (CONH₂), fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,    difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,    trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine or    chlorine,-   R^(2b) very particularly preferably represents a group selected from    Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15,    Q16 and Q17,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent methyl, ethyl, isopropyl, tert-butyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent methyl,        ethyl, isopropyl, tert-butyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R³ very particularly preferably represents fluorine, chlorine,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulphonyl or    trifluoromethylsulphinyl,-   R⁴ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine or cyano,-   R⁵ very particularly preferably represents methyl, ethyl, isopropyl,    methoxymethyl or methoxyethyl,-   R⁸ very particularly preferably represents hydrogen, represents    methyl, ethyl, isopropyl, tert-butyl, methoxy or ethoxy, each of    which is optionally monosubstituted by halogen, cyano, phenyl or    pyridyl, where phenyl and pyridyl may each be mono- or disubstituted    by identical or different substituents from the group consisting of    trifluoromethyl, cyano, fluorine, chlorine, bromine and    trifluoromethoxy, or-   R⁸ very particularly preferably represents phenyl, pyridyl or a 3-    to 6-membered saturated heterocycle comprising 1-2 heteroatoms from    the group consisting of N, S and O, where phenyl, pyridyl and the    heterocycle may each optionally be mono- or disubstituted by    identical or different substituents, and where the substituents    independently of one another may be selected from C₁-C₄-alkyl,    C₁-C₄-haloalkyl, halogen and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another very particularly    preferably represent methyl, ethyl, isopropyl or tert-butyl, each of    which may optionally be monosubstituted by halogen, cyano, phenyl or    pyridyl, where phenyl and pyridyl may each optionally be mono- or    disubstituted by identical or different substituents from the group    consisting of trifluoromethyl, cyano, fluorine, chlorine and    trifluoromethoxy, or-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another very particularly    preferably represent phenyl, pyridyl or a 3- to 6-membered saturated    heterocycle comprising 1-2 heteroatoms from the group consisting of    N, S and O, where phenyl, pyridyl and the heterocycle may each be    mono- or disubstituted by identical or different substituents, and    where the substituents independently of one another may be selected    from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen    and cyano,-   R¹¹, R¹² independently of one another very particularly preferably    represent hydrogen or represent R⁹,-   m very particularly preferably represents 0, 1 or 2,-   n very particularly preferably represents 0, 1 or 2,-   p very particularly preferably represents 0 and 1.    Configuration 4-1:-   A¹ very particularly preferably represents nitrogen or ═C—R⁴,-   A² very particularly preferably represents —N—R⁵ or oxygen,-   A⁴ very particularly preferably represents ═C—H,-   R¹ very particularly preferably represents methyl, ethyl, n-propyl,    isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    benzyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R^(2a) very particularly preferably represents hydrogen, cyano,    aminocarbonyl (CONH₂), fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,    difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,    trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine or    chlorine,-   R^(2b) very particularly preferably represents a group selected from    Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15,    Q16 and Q17,    -   where, if R^(2b) represents Q12 and R¹¹ represents hydrogen, R⁸        does not represent methyl, ethyl, isopropyl, tert-butyl,    -   where, if R^(2b) represents Q17, R¹³ does not represent methyl,        ethyl, isopropyl, tert-butyl,    -   where, if R^(2b) represents Q5, Q6, Q7, Q8 or Q9, n represents        2,-   R³ very particularly preferably represents fluorine, chlorine,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulphonyl or    trifluoromethylsulphinyl,-   R⁴ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine or cyano,-   R⁵ very particularly preferably represents methyl, ethyl, isopropyl,    methoxymethyl or methoxyethyl,-   R⁸ very particularly preferably represents hydrogen, represents    methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,    difluoromethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl,    cyclopropyl, cyclopropylmethyl, methoxy or ethoxy, or-   R⁸ very particularly preferably represents phenyl, pyridyl or    pyrazolyl, where phenyl, pyridyl and pyrazolyl may in each case    optionally be mono- or disubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, halogen and cyano,-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another very particularly    preferably represent methyl, ethyl, isopropyl, tert-butyl, benzyl or    methylsulphonyl, or-   R⁹, R¹³, R¹⁴, R¹⁵ independently of one another very particularly    preferably represent phenyl, pyridyl or pyrazolyl, where phenyl,    pyridyl and pyrazolyl may in each case optionally be mono- or    disubstituted by identical or different substituents, and where the    substituents independently of one another may be selected from the    group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen and cyano,-   R¹¹, R¹² independently of one another very particularly preferably    represent hydrogen or represent R⁹,-   m very particularly preferably represents 0, 1 or 2,-   n very particularly preferably represents 0, 1 or 2,-   p very particularly preferably represents 0 and 1.    Configuration 4-2:-   A¹ very particularly preferably represents nitrogen or ═C—R⁴,-   A² very particularly preferably represents —N—R⁵ or oxygen,-   A⁴ very particularly preferably represents ═C—H,-   R¹ very particularly preferably represents methyl, ethyl, n-propyl,    isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    benzyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R^(2a) very particularly preferably represents hydrogen, cyano,    aminocarbonyl (CONH₂), fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,    difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,    trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine or    chlorine,-   R^(2b) very particularly preferably represents a group selected from    -   Q1, where R⁸ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl, methoxy or ethoxy,    -   Q3, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl or cyclopropyl and R¹² represents hydrogen, methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,        cyclopropyl or acetyl,    -   Q4, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl or cyclopropyl and R¹² represents hydrogen, methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,        cyclopropyl or acetyl,    -   Q5, where m represents 0, 1 or 2 and R¹³ represents methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,        phenyl or benzyl,    -   Q6, where R¹³ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl or tert-butyl,    -   Q8, where R¹³ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl or tert-butyl,    -   Q9, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl or cyclopropyl and R¹² represents hydrogen, methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,        cyclopropyl or acetyl,    -   Q10, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl and R¹²        represents hydrogen, methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl, tert-butyl or cyclopropyl,    -   Q11, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl, cyclopropyl or acetyl and R¹² represents hydrogen,        methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,        tert-butyl, cyclopropyl, phenyl or acetyl,    -   Q12, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl or cyclopropyl and R⁸ represents methyl, ethyl,        n-propyl, isopropyl (only if R¹¹ does not represent hydrogen may        R⁸ represent methyl, ethyl, n-propyl or isopropyl),        fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,        difluoroethyl, trifluoroethyl, tetrafluoroethyl,        pentafluoroethyl, CH₂OCH₃, CH₂SCH₃, CH₂OC₂H₅, CH₂SOCH₃,        CH₂SO₂CH₃, CH(CH₃)CH₂SCH₃, CH(CH₃)CH₂SOCH₃, CH(CH₃)CH₂SO₂CH₃,        C₂H₄OC₂H₅, C₂H₄SC₂H₅, C₂H₄OC₂H₅, C₂H₄SOC₂H₅, C₂H₄SO₂C₂H₅,        CH(CH₃)CH₂SC₂H₅, CH(CH₃)CH₂SOC₂H₅, CH(CH₃)CH₂SO₂C₂H₅,        cyclopropyl, cyclopropylmethyl, represents phenyl, benzyl,        pyridyl or thiazolyl, each of which may optionally be        monosubstituted by fluorine, chlorine or bromine,    -   Q13, where R⁸ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl or tert-butyl and R¹¹ represents hydrogen,        methyl, ethyl, n-propyl, isopropyl or cyclopropyl,    -   Q14, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl, methylsulphonyl or cyclopropyl and R¹³ represents        methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,        tert-butyl, cyclopropyl, fluoromethyl, difluoromethyl,        trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,        tetrafluoroethyl or pentafluoroethyl,    -   Q17, where R¹³ represents pyrazolyl which is optionally        monosubstituted by trifluoromethyl,    -   Q18, where R⁸ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl, tert-butyl, cyclopropyl or phenyl, R¹¹        represents hydrogen, methyl or ethyl and R¹² represents        hydrogen, methyl or ethyl,    -   where, if R^(2b) represents Q5, Q6, Q8 or Q9, n represents 2,-   R³ very particularly preferably represents fluorine, chlorine,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulphonyl or    trifluoromethylsulphinyl,-   R⁴ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine or cyano,-   R⁵ very particularly preferably represents methyl, ethyl, isopropyl,    methoxymethyl or methoxyethyl,-   n very particularly preferably represents 0, 1 or 2.    Configuration 5:-   A¹ with emphasis represents nitrogen,-   A² with emphasis represents —N—R⁵,-   A⁴ with emphasis represents ═C—H,-   R¹ with emphasis represents ethyl or benzyl,-   R^(2a) with emphasis represents hydrogen,-   R^(2b) with emphasis represents a group selected from    -   Q1, where R⁸ represents methoxy,    -   Q5, where m represents 0 or 2 and R¹³ represents methyl, ethyl        or isopropyl,    -   Q10, where R¹¹ represents hydrogen or methylsulphonyl and R¹²        represents hydrogen or methylsulphonyl,    -   Q12, where R¹¹ represents hydrogen and R⁸ represents        trifluoromethyl, CHF₂, CF₂CF₃, CF₂CHF₂, CH₂OCH₃, cyclopropyl,        cyclopropylmethyl (—CH₂-cyclopropyl) or phenyl,    -   Q14, where R¹¹ represents hydrogen and R¹³ represents methyl,    -   Q17, where R¹³ represents trifluoromethyl-1H-pyrazol-5-yl,    -   where, if R^(2b) represents Q5, n represents 2,-   R³ with emphasis represents trifluoromethyl,-   R⁵ with emphasis represents methyl,-   n with emphasis represents 0, 1 or 2.    Configuration 5-2a:-   A¹ with emphasis represents nitrogen,-   A² with emphasis represents —N—R⁵,-   A⁴ with emphasis represents ═C—H,-   R¹ with emphasis represents methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl or tert-butyl,-   R^(2a) with emphasis represents hydrogen,-   R^(2b) with emphasis represents a group selected from    -   Q1, where R⁸ represents methoxy or ethoxy,    -   Q3, where R¹¹ represents hydrogen or methyl and R¹² represents        hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,        tert-butyl or cyclopropyl,    -   Q4, where R¹¹ represents hydrogen or methyl and R¹² represents        methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,        tert-butyl or cyclopropyl,    -   Q5, where m represents 0, 1 or 2 and R¹³ represents methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,        phenyl or benzyl,    -   Q6, where R¹³ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl or tert-butyl,    -   Q8, where R¹³ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl or tert-butyl,    -   Q9, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl or cyclopropyl and R² represents hydrogen, methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or        cyclopropyl,    -   Q10, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl or cyclopropyl and R¹² represents hydrogen, methyl,        ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or        cyclopropyl,    -   Q11, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl, cyclopropyl or COmethyl (acetyl) and R¹² represents        hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,        tert-butyl, cyclopropyl or COmethyl (acetyl),    -   Q12, where R¹¹ represents hydrogen or methyl and R⁸ represents        methyl, ethyl, n-propyl, isopropyl (only if R¹¹ does not        represent hydrogen may R⁸ represent methyl, ethyl, n-propyl,        isopropyl), trifluoromethyl, CHF₂, CF₂CF₃, CF₂CHF₂, CH₂OCH₃,        CH₂SCH₃, CH₂OC₂H₅, CH₂SOCH₃, CH₂SO₂CH₃, CH(CH₃)CH₂SCH₃,        CH(CH₃)CH₂SOCH₃, CH(CH₃)CH₂SO₂CH₃, C₂H₄OC₂H₅, C₂H₄SC₂H₅,        C₂H₄OC₂H₅, C₂H₄SOC₂H₅, C₂H₄SO₂C₂H₅, CH(CH₃)CH₂SC₂H₅,        CH(CH₃)CH₂SOC₂H₅, CH(CH₃)CH₂SO₂C₂H₅, cyclopropyl,        cyclopropylmethyl (—CH₂-cyclopropyl), phenyl, benzyl,

-   -   Q13, where R⁸ represents methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl, tert-butyl or cyclopropyl and R¹¹ represents        hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl,    -   Q14, where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,        isopropyl, methylsulphonyl or cyclopropyl and R¹³ represents        methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,        tert-butyl, cyclopropyl or trifluoromethyl,    -   Q17, where R¹³ represents trifluoromethyl-1H-pyrazol-5-yl

-   -   Q18, where R⁸ represents cyclopropyl, R¹¹ represents hydrogen,        methyl or ethyl and R¹² represents hydrogen, methyl or ethyl,    -   where, if R^(2b) represents Q5, Q6, Q8 or Q9, n represents 2,

-   R³ with emphasis represents fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl or pentafluoroethyl,

-   R⁵ with emphasis represents methyl, ethyl or isopropyl,

-   n with emphasis represents 0, 1 or 2.    Configuration 5-2b:

-   A¹ with emphasis represents nitrogen,

-   A² with emphasis represents —N—R⁵,

-   A⁴ with emphasis represents ═C—H,

-   R¹ with emphasis represents ethyl,

-   R^(2a) with emphasis represents hydrogen,

-   R^(2b) with emphasis represents a group selected from    -   Q1, where R⁸ represents methoxy,    -   Q3, where R¹¹ represents hydrogen and R¹² represents hydrogen,        methyl, ethyl or cyclopropyl,    -   Q4, where R¹¹ represents hydrogen and R¹² represents methyl,        ethyl or cyclopropyl,    -   Q5, where m represents 0, 1 or 2 and R¹³ represents methyl,        ethyl, isopropyl, phenyl or benzyl,    -   Q6, where R¹³ represents ethyl,    -   Q8, where R¹³ represents methyl,    -   Q9, where R¹¹ represents hydrogen or methyl and R¹² represents        methyl, ethyl or isopropyl,    -   Q10, where R¹¹ represents hydrogen or methyl and R¹² represents        hydrogen, methyl or ethyl,    -   Q11, where R¹¹ represents hydrogen, methyl or COmethyl (acetyl)        and R¹² represents hydrogen, methyl or COmethyl (acetyl),    -   Q12, where R¹¹ represents hydrogen or methyl and R⁸ represents        methyl (only if R¹¹ does not represent hydrogen),        trifluoromethyl, CHF₂, CF₂CF₃, CF₂CHF₂, CH₂OCH₃, CH₂SCH₃,        CH₂OC₂H₅, CH₂SOCH₃, CH₂SO₂CH₃, CH(CH₃)CH₂SCH₃, CH(CH₃) CH₂SOCH₃,        CH(CH₃)CH₂SO₂CH₃, cyclopropyl, cyclopropylmethyl        (—CH₂-cyclopropyl), phenyl, benzyl,

-   -   Q13, where R⁸ represents methyl and R¹¹ represents hydrogen,    -   Q14, where R¹¹ represents hydrogen or methylsulphonyl and R³        represents methyl, ethyl or trifluoromethyl,    -   Q17, where R¹³ represents trifluoromethyl-1H-pyrazol-5-yl

-   -   Q18, where R⁸ represents cyclopropyl, R¹¹ represents hydrogen        and R² represents hydrogen,    -   where, if R^(2b) represents Q5, Q6, Q8 or Q9, n represents 2,

-   R³ with emphasis represents trifluoromethyl or pentafluoroethyl,

-   R⁵ with emphasis represents methyl,

-   n with emphasis represents 0, 1 or 2.    Configuration 6-2a:

-   A¹ especially represents nitrogen,

-   A² especially represents —N—R⁵,

-   A⁴ especially represents ═C—H,

-   R¹ especially represents methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl or tert-butyl,

-   R^(2a) especially represents hydrogen,

-   R^(2b) especially represents a group selected from

-   R³ especially represents fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl or pentafluoroethyl,-   R⁵ especially represents methyl, ethyl or isopropyl,-   n especially represents 0 or 2, where, if R^(2b) represents Q5a-j,    Q6a, Q8a, Q9a-d, then n represents 2.    Configuration 6-2b:-   A¹ especially represents nitrogen,-   A² especially represents —N—R⁵,-   A⁴ especially represents ═C—H,-   R¹ especially represents ethyl,-   R^(2a) especially represents hydrogen,-   R^(2b) has the meanings given in Configuration (6-2a),-   R³ especially represents trifluoromethyl or pentafluoroethyl,-   R⁵ especially represents methyl,-   n especially represents 0 or 2, where, if R^(2b) represents Q5a-j,    Q6a, Q8a, Q9a-d, then n represents 2.

A¹ represents ═N⁺—O⁻ means ═N⁺(O⁻)—; A¹ represents ═C—R⁴ means ═C(R⁴)—(identical to CR⁴), A² represents —N—R⁵ means —N(R⁵)— (identical toN—R⁵); A⁴ represents ═N⁺—O⁻ means ═N⁺(O⁻)—; A⁴ represents ═C—R⁴ means═C(R⁴)— (identical to CR⁴).

If R^(2b) represents Q11 (—NR¹¹—NR¹¹R¹²), then R¹¹ at one of thenitrogen atoms may have a meaning different from that at the othernitrogen atom, for example in compound 74 where R¹¹ at one of thenitrogen atoms represents methyl and at the other nitrogen atomrepresents hydrogen, R¹² in compound 74 represents hydrogen.

In a further embodiment, the invention relates to compounds of theformula (I-A)

where R¹, R^(2a), R^(2b), R³, R⁵ and n have the meanings describedabove, in particular the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5) orconfiguration (5-2a) or configuration (5-2b) or configuration (6-2a) orconfiguration (6-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q1 and R¹, R^(2a), R³, R⁵, R⁸ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q2 and R¹, R^(2a), R³, R⁵, R⁸ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q3 and R¹, R^(2a), R³, R⁵, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q4 and R¹, R², R³, R⁵, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q5 and R¹, R^(2a), R³, R⁵, R¹³, mand n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q6 and R¹, R^(2a), R³, R⁵, R¹³ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q7 and R¹, R^(2a), R³, R⁵, R¹³ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (3)or configuration (3-1) or configuration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q8 and R¹, R^(2a), R³, R⁵, R¹³ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q9 and R¹, R², R³, R⁵, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q10 and R¹, R^(2a), R³, R⁵, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q11 and R¹, R^(2a), R³, R⁵, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q12 and R¹, R^(2a), R³, R⁵, R⁸,R¹¹ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q13 and R¹, R², R³, R⁵, R⁸, R¹¹and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q14 and R¹, R², R³, R⁵, R¹¹, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q15 and R¹, R², R³, R⁵, R¹¹, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q16 and R¹, R², R³, R⁵, R¹⁴, R¹⁵and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q17 and R¹, R^(2a), R³, R⁵, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2) orconfiguration (5) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-A) where R^(2b) represents Q18 and R¹, R^(2a), R³, R⁵, R⁸,R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1-2) or configuration (2-2) orconfiguration (3-2) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I-B)

where R¹, R^(2a), R^(2b), R³ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q1 and R¹, R^(2a), R³, R⁸ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (2-2) orconfiguration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q2 and R¹, R^(2a), R³, R⁸ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (2-2) orconfiguration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q3 and R¹, R^(2a), R³, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q4 and R¹, R^(2a), R⁵, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q5 and R¹, R^(2a), R³, R¹³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (2-2) orconfiguration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q6 and R¹, R^(2a), R³, R¹³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (2-2) orconfiguration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q7 and R¹, R^(2a), R³, R¹³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (3) orconfiguration (3-1) or configuration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q8 and R¹, R^(2a), R³, R¹³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (2-2) orconfiguration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q9 and R¹, R^(2a), R³, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q10 and R¹, R^(2a), R³, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q11 and R¹, R^(2a), R³, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q12 and R¹, R^(2a), R³, R⁸, R¹¹and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q13 and R¹, R^(2a), R³, R⁸, R¹¹and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q14 and R¹, R^(2a), R³, R¹¹, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q15 and R¹, R^(2a), R³, R¹¹, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q16 and R¹, R², R³, R¹⁴, R¹⁵, pand n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q17 and R¹, R², R³, R¹³ and n havethe meanings described above, in particular the meanings described inconfiguration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (2-2) orconfiguration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-B) where R^(2b) represents Q18 and R¹, R^(2a), R³, R⁸, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1-2) or configuration (2-2) or configuration(3-2) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C)

where R¹, R^(2a), R^(2b), R³, R⁴, R⁵ and n have the meanings describedabove, in particular the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q1 and R¹, R^(2a), R³, R⁴, R⁵, R⁸and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q2 and R¹, R^(2a), R³, R⁴, R⁵, R⁸and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q3 and R¹, R^(2a), R³, R⁴, R⁵,R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q4 and R¹, R^(2a), R³, R⁴, R⁵,R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q5 and R¹, R^(2a), R³, R⁴, R⁵,R¹³, m and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q6 and R¹, R^(2a), R³, R⁴, R⁵, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q7 and R¹, R^(2a), R³, R⁵, R¹³ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (3)or configuration (3-1) or configuration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q8 and R¹, R^(2a), R³, R⁴, R⁵, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q9 and R¹, R^(2a), R³, R⁵, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q10 and R¹, R^(2a), R³, R⁴, R⁵,R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q11 and R¹, R^(2a), R³, R⁴, R⁵,R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q12 and R¹, R^(2a), R³, R⁴, R⁵,R⁸, R¹¹ and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q13 and R¹, R², R³, R⁴, R⁵, R⁸,R¹¹ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q14 and R¹, R², R³, R⁴, R⁵, R¹¹,R¹³ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q15 and R¹, R², R³, R⁴, R⁵, R¹¹,R¹³ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q16 and R¹, R², R³, R⁵, R¹⁴, R¹⁵,p and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q17 and R¹, R^(2a), R³, R⁴, R⁵,R¹³ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-C) where R^(2b) represents Q18 and R¹, R^(2a), R³, R⁴, R⁵,R⁸, R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1-2) or configuration (2-2) orconfiguration (3-2) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D)

where R¹, R^(2a), R^(2b), R³, R⁴ and n have the meanings describedabove, in particular the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q1 and R¹, R^(2a), R³, R⁴, R⁸ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q2 and R¹, R^(2a), R³, R⁴, R⁸ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q3 and R¹, R^(2a), R³, R⁴, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q4 and R¹, R^(2a), R³, R⁴, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q5 and R¹, R^(2a), R³, R⁴, R¹³, mand n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q6 and R¹, R^(2a), R³, R⁴, R¹³ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q7 and R¹, R^(2a), R³, R¹³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (1-2) orconfiguration (2) or configuration (2-1) or configuration (3) orconfiguration (3-1) or configuration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q8 and R¹, R^(2a), R³, R⁴, R¹³ andn have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q9 and R¹, R^(2a), R³, R¹¹, R¹²and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q10 and R¹, R^(2a), R³, R⁴, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q11 and R¹, R^(2a), R³, R⁴, R¹¹,R¹² and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q12 and R¹, R^(2a), R³, R⁴, R⁸,R¹¹ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q13 and R¹, R^(2a), R³, R⁴, R⁸,R¹¹ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q14 and R¹, R^(2a), R³, R⁴, R¹¹,R¹³ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q15 and R¹, R^(2a), R³, R⁴, R¹¹,R¹³ and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q16 and R¹, R², R³, R¹⁴, R¹⁵, pand n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q17 and R¹, R^(2a), R³, R⁴, R¹³and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(1-2) or configuration (2) or configuration (2-1) or configuration (2-2)or configuration (3) or configuration (3-1) or configuration (3-2) orconfiguration (4) or configuration (4-1) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I-D) where R^(2b) represents Q18 and R¹, R^(2a), R³, R⁴, R⁸,R¹¹, R¹² and n have the meanings described above, in particular themeanings described in configuration (1-2) or configuration (2-2) orconfiguration (3-2) or configuration (4-2).

In a further embodiment, the invention relates to compounds of theformula (I(Q1))

where R^(2b) represents —C(═O)—R⁸ (Q1) and where R¹, R^(2a), R³, R⁸, A¹,A², A⁴ and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q2))

where R^(2b) represents —C(═S)—R⁸ (Q2) and where R¹, R^(2a), R³, R⁸, A¹,A², A⁴ and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I(Q3))

where R^(2b) represents —C(═O)—NR¹¹R¹² (Q3) and where R¹, R^(2a), R³,R¹¹, R¹², A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q4))

where R^(2b) represents —C(═S)—NR¹¹R¹² (Q4) and where R¹, R^(2a), R³,R¹¹, R¹², A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q5))

where R^(2b) represents —S(O)_(m)—R¹³ (Q5) and where R¹, R^(2a), R³,R¹³, A¹, A², A⁴, m and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q6))

where R^(2b) represents —S═O(═NH)—R¹³ (Q6) and where R¹, R^(2a), R³,R¹³, A¹, A², A⁴ and n have the meanings described above, in particularthe meanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q7))

where R^(2b) represents —S═O(═N—CN)—R¹³ (Q7) and where R¹, R^(2a), R³,R¹³, A¹, A², A⁴ and n have the meanings described above, in particularthe meanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (3) or configuration (3-1) or configuration (4) orconfiguration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I(Q8))

where R^(2b) represents —S(═N—CN)—R¹³ (Q8) and where R¹, R^(2a), R³,R¹³, A¹, A², A⁴ and n have the meanings described above, in particularthe meanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q9))

where R^(2b) represents —S(O)₂—NR¹¹R¹² (Q9) and where R¹, R^(2a), R³,R¹¹, R¹², A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q10))

where R^(2b) represents —NR¹¹R¹² (Q10) and where R¹, R^(2a), R³, R¹¹,R¹², A¹, A², A⁴ and n have the meanings described above, in particularthe meanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q11))

where R^(2b) represents —NR¹¹—NR¹¹R¹² (Q11) and where R¹, R^(2a), R³,R¹¹, R¹², A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q12))

where R^(2b) represents —NR¹¹—C(═O)—R⁸ (Q12) and where R¹, R^(2a), R³,R⁸, R¹¹, A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q13))

where R^(2b) represents —NR¹¹—C(═S)—R⁸ (Q13) and where R¹, R^(2a), R³,R⁸, R¹¹, A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q14))

where R^(2b) represents —NR¹¹—S(O)₂—R³ (Q14) and where R¹, R^(2a), R³,R¹¹, R¹³, A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q15))

where R^(2b) represents —N(R¹¹)—O—R¹³ (Q15) and where R¹, R^(2a), R³,R¹¹, R¹³, A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I(Q16))

where R^(2b) represents —N═S(O)_(p)—R¹⁴R¹⁵ (Q16) and where R¹, R^(2a),R³, R¹¹, R¹³, A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(1-1) or configuration (1-2) or configuration (2) or configuration (2-1)or configuration (2-2) or configuration (3) or configuration (3-1) orconfiguration (4) or configuration (4-1).

In a further embodiment, the invention relates to compounds of theformula (I(Q17))

where R^(2b) represents —O—R¹³ (Q17) and where R¹, R^(2a), R³, R¹³, A¹,A², A⁴ and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (1-2) or configuration (2) or configuration (2-1) orconfiguration (2-2) or configuration (3) or configuration (3-1) orconfiguration (3-2) or configuration (4) or configuration (4-1) orconfiguration (4-2) or configuration (5) or configuration (5-2a) orconfiguration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I(Q18))

where R^(2b) represents —CR¹¹═CR⁸R¹² (Q18) and where R¹, R^(2a), R³, R⁸,R¹¹, R¹², A¹, A², A⁴ and n have the meanings described above, inparticular the meanings described in configuration (1-2) orconfiguration (2-2) or configuration (3-2) or configuration (4-2) orconfiguration (5-2a) or configuration (5-2b).

In a further embodiment, the invention relates to compounds of theformula (I) where R¹, R^(2a), R³, R⁸, R¹¹, R¹², A¹, A², A⁴ and n havethe meanings described above, in particular the meanings described inconfiguration (1) or configuration (1-1) or configuration (2) orconfiguration (2-1) or configuration (3) or configuration (3-1) orconfiguration (4) or configuration (4-1) and R^(2b) represents a groupselected from Q1, Q2, Q3 and Q4.

In a further embodiment, the invention relates to compounds of theformula (I) where R¹, R^(2a), R³, R¹¹, R¹², R¹³, A¹, A², A⁴, m and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (1-1) or configuration (2) orconfiguration (2-1) or configuration (3) or configuration (3-1) orconfiguration (4) or configuration (4-1) and R^(2b) represents a groupselected from Q5, Q6, Q7, Q8 and Q9.

In a further embodiment, the invention relates to compounds of theformula (I) where R¹, R^(2a), R³, R⁸, R¹, R¹², R¹³, R¹⁴, R⁵, A¹, A², A⁴,p and n have the meanings described above, in particular the meaningsdescribed in configuration (1) or configuration (1-1) or configuration(2) or configuration (2-1) or configuration (3) or configuration (3-1)or configuration (4) or configuration (4-1) and R^(2b) represents agroup selected from Q10, Q11, Q12, Q13, Q14, Q15 and Q16.

In a further embodiment, the invention relates to compounds of theformula (I) where R¹, R^(2a), R³, R⁸, R¹¹, R¹², R³, R¹⁴, R¹⁵, A¹, A²,A⁴, p and n have the meanings described above, in particular themeanings described in configuration (1) or configuration (1-1) orconfiguration (2) or configuration (2-1) or configuration (3) orconfiguration (3-1) or configuration (4) or configuration (4-1) and R2brepresents a group selected from Q10, Q11, Q13, Q14, Q15 and Q16.

In a further embodiment, the invention relates to compounds of theformula (I) where R¹, R^(2a), R³, R¹³, A¹, A², A⁴ and n have themeanings described above, in particular the meanings described inconfiguration (1) or configuration (1-1) or configuration (2) orconfiguration (2-1) or configuration (3) or configuration (3-1) orconfiguration (4) or configuration (4-1) or configuration (5) and R^(2b)represents a group selected from Q17.

In the preferred definitions, unless stated otherwise,

halogen is selected from the group consisting of fluorine, chlorine,bromine and iodine, preferably in turn from the group consisting offluorine, chlorine and bromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group consisting of phenyl, naphthyl, anthryl,phenanthrenyl, and is preferably in turn phenyl,

hetaryl (synonymous with heteroaryl or aromatic heterocycle, includingas part of a larger unit, for example hetarylalkyl) is selected from thegroup consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, pyridyl, pyrimidyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl,indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl,benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole,quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl andindolizinyl,heterocyclyl is a saturated 3-, 4-, 5- or 6-membered ring containing 1or 2 nitrogen atoms and/or one oxygen atom and/or one sulphur atom, forexample aziridinyl, oxiranyl, thiiranyl, azetidinyl, pyrrolidinyl,piperidinyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl,thietanyl, tetrahydrothiophenyl, tetrahydrothiopyranyl, piperazinyl,morpholinyl and thiomorpholinyl.

In the particularly preferred definitions, unless stated otherwise,

halogen is selected from the group consisting of fluorine, chlorine,bromine and iodine, preferably in turn from the group consisting offluorine, chlorine and bromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group consisting of phenyl, naphthyl, anthryl,phenanthrenyl, and is preferably in turn phenyl,

hetaryl (including as part of a larger unit, for example hetarylalkyl)is selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl,pyridazinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl and tetrazolyl,

heterocyclyl is selected from the group consisting of oxetanyl,tetrahydrofuryl and piperazinyl.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. From amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl.

Among these, preference is given to C₃-C₆-alkynyl radicals andparticular preference to C₃-C₄-alkynyl radicals. The alkynyl radical mayalso contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood to mean an O-alkyl radical,where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms can be identical ordifferent. In this case, halogen is fluorine, chlorine, bromine oriodine, especially fluorine, chlorine or bromine.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionmay be the same or different.

The radical definitions or elucidations given above in general terms orwithin areas of preference apply to the end products and correspondinglyto the starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference according to the invention is given to using compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of thedefinitions listed above as being very particularly preferred.

Emphasis according to the invention is given to using compounds of theformula (I) which contain a combination of the meanings listed above asbeing emphasized.

Special emphasis according to the invention is given to using compoundsof the formula (I) which contain a combination of the meanings listedabove as being especially emphasized.

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. Accordingly, the inventionencompasses both pure stereoisomers and any mixtures of these isomers.

The compounds of the formula (I) according to the invention can beobtained by the processes shown in the following schemes:

Process A

The radicals R¹, R^(2a), R³, R¹¹, R¹², A¹, A², A⁴ and n have themeanings described above and X¹ represents halogen and V represents(C₁-C₄)-alkyl.

Step a)

The compounds of the formula (IV) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula (III)in the presence of a condensing agent.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (III) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure and at temperatures of 0 to 180° C.;with preference, the reaction is carried out at atmospheric pressure andtemperatures of 20 to 140° C.

Step b)

The compounds of the formula (V) can be prepared by condensing thecompounds of the formula (IV), for example analogously to the processesdescribed in WO2012/86848.

The conversion to compounds of the formula (V) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (VI) can be prepared by halogenating thecompounds of the formula (V), for example analogously to the processesdescribed in U.S. Pat. No. 4,801,593. An example of a suitablehalogenating agent is phosphorus oxychloride. Useful solvents ordiluents include all inert organic solvents, for example aliphatic oraromatic hydrocarbons. Preference is given to using toluene.

In a further embodiment, the nitrogen (A¹=N) in the vicinity of thehalogenation position is initially oxidized, for example analogously tothe processes described in WO2008/112646. Examples of suitable oxidizingagents are meta-chloroperbenzoic acid and hydrogen peroxide. Thereaction is preferably carried out in a solvent selected from customarysolvents which are inert under the prevailing reaction conditions.Preference is given to halogenated hydrocarbons such as, for example,dichloromethane, chloroform, or to esters such as ethyl acetate. Thesubsequent halogenation is carried out as described above using asuitable halogenating agent such as, for example, phosphorusoxychloride.

Step d)

The compounds of the formula (XIV) can be prepared by carbonylation ofthe compounds of the formula (VI) analogously to S. A. Vinogradov, D. F.Wilson, Tetrahedron Letters 39 (1998), 8935-8938. The radical V ispreferably methyl, ethyl, n-propyl or n-butyl. Suitable for use ascatalysts for reaction d) are palladium phosphane complexes, for examplea catalyst of palladium chloride, triphenylphosphane and DPPP(1,3-bis(diphenylphosphino)propane) (1:1:1). Preferred bases are, forexample, Hünig's base (diisopropylethylamine) or DBU(1,8-diazabicyclo[5.4.0]undec-7-ene).

Steps e, f, g)

The ester of the formula (XIV) can be converted by standard methods, cf.DE 2221647, first into the acid of the formula (XV), for example usingan alkali metal hydroxide such as sodium hydroxide or lithium hydroxideas base in an alcohol such as, for example, ethanol or a mixture oftetrahydrofuran and water as solvent.

The acid of the formula (XV) is then converted by standard methods intothe acid chloride of the formula (XVI), for example using a chlorinatingagent such as thionyl chloride or oxalyl chloride.

Further reaction with the amine of the formula (XVII) in a diluent suchas, for example, dichloromethane or tetrahydrofuran, and in the presenceof a base such as, for example, triethylamine or diisopropylethylamine,affords the compounds of the formula (Ia) (corresponds to formula I(Q3))according to the invention.

Compounds of the formula (XVII) are either commercially available or canbe prepared by known methods.

Step h)

Thioamides of the formula (Ib) (corresponds to formula I(Q4)) can beprepared from the carboxamides of the formula (Ia) by reaction with asulfurizing agent, for example Lawesson's reagent or P₄S₁₀.

Process B

The radicals R¹, R^(2a), R³, A¹, A², A⁴ and n have the meaningsdescribed above.

In a further embodiment of the invention, compounds of the formula (V)can be prepared in a one-stage process from the compounds of the formula(II) using compounds of the formula (III) in the presence of acondensing agent.

The conversion to compounds of the formula (V) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol, ethanolor isopropanol; nitriles, for example acetonitrile or propionitrile;aromatic hydrocarbons, for example toluene or xylene; aprotic polarsolvents, for example N,N-dimethylformamide or N-methylpyrrolidone, ornitrogen compounds, for example pyridine.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

The reaction can be carried out in the presence of an acid or a base.

Examples of an acid which can be used in the reaction described aresulphonic acids such as methanesulphonic acid or para-toluenesulphonicacid; carboxylic acids such as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

The reaction can be carried out in the presence of a suitable catalyst,for example 1-hydroxybenzotriazole.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

The further conversion of the compounds of the formula (V) to compoundsof the formula (I) is carried out analogously to process A.

Process C

The radical R¹, R^(2a), R^(2b), R³, A¹, A² and A⁴ have the meaningsdescribed above and X¹ and X² represent halogen.

Step a)

The compounds of the formula (VIII) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with a carboxylic acid of the formula(VII) in the presence of a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (VII) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (VII) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure and at temperatures of 0 to 180° C.;with preference, the reaction is carried out at atmospheric pressure andtemperatures of 20 to 140° C.

Step b)

The compounds of the formula (IX) can be prepared by condensing theintermediates of the formula (VIII), for example analogously to theprocesses described in WO2012/86848.

The conversion to compounds of the formula (IX) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (XI) can be prepared by reacting thecompounds of the formula (IX) with the compounds of the formula (X) inthe presence of a base.

Mercaptan derivatives of the formula (X), for example methyl mercaptan,ethyl mercaptan or isopropyl mercaptan, are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in US2006/25633, US2006/111591, U.S. Pat. No.2,820,062, Chemical Communications, 13 (2000), 1163-1164 or Journal ofthe American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (XI) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given to caesium carbonate, sodium carbonateand potassium carbonate. Further suitable bases are alkali metalhydrides, for example sodium hydride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step d)

The compounds of the formula (XII) can be prepared by oxidizing thecompounds of the formula (XI). The oxidation is generally carried out ina solvent selected from customary solvents which are inert under theprevailing reaction conditions. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (XIII) can be prepared by oxidizing thecompounds of the formula (XII). The oxidation is generally carried outin a solvent. Preference is given to halogenated hydrocarbons, forexample dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol orethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step f)

The compounds of the formula (XIII) can also be prepared in a one-stepprocess by oxidizing the compounds of the formula (XI). The oxidation isgenerally carried out in a solvent. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step g)

The further conversion of the compounds of the formula (XIII) tocompounds of the formula (I) is carried out analogously to process A.

The compounds of the formulae (XI) and (XII) can be convertedanalogously to process A to compounds of the formula (I).

Process D

The radicals R¹, R^(2a), R³, R⁸, R¹⁴, R⁵, A¹, A², A⁴ and n have themeanings described above and X¹ represents halogen.

Step a)

The compounds of the formula (XVIII) can be prepared analogously toWO2015/002211 by reacting the compounds of the formula (VI) with sodiumazide.

The conversion to compounds of the formula (XIII) is usually carried outin a solvent, preference being given to carrying out the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers such as,for example, tetrahydrofuran, ethylene glycol dimethyl ether, dioxane,aprotic polar solvents such as, for example, N,N-dimethylformamide,N-methylpyrrolidone, dimethyl sulphoxide, or alcohols such as methanolor ethanol.

Step b)

The compounds of the formula (XIX) can be prepared by reducing theintermediates of the formula (XVIII), for example analogously to theprocesses described in WO2015/002211.

Examples of suitable reducing agents are triphenylphosphine,tributylphosphine, tin(III) chloride and zinc.

The conversion to compounds of the formula (XIX) is generally carriedout in a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, ethylene glycol dimethyl ether, dioxane, aliphatichydrocarbons such as hexane, heptane, aromatic hydrocarbons such astoluene, xylene, halogenated hydrocarbons such as, for example,dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene, aprotic polar solvents such as, for example,N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulphoxide, oralcohols such as methanol or ethanol.

If required, an acid such as, for example, hydrochloric acid or aceticacid may be added to the reaction.

Step c)

The compounds of the formula (XXI) can be prepared by reacting thecompounds of the formula (XIX) with a compound of the formula (XX) inthe presence of an oxidizing agent.

Compounds of the formula (XX) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (XXI) (corresponds to formulaI(Q16) where p=0) is generally carried out in a solvent. Preference isgiven to ethers such as, for example, tetrahydrofuran, methyl tert-butylether, dioxane, aliphatic hydrocarbons such as hexane, heptane, aromatichydrocarbons such as toluene, xylene, halogenated hydrocarbons such as,for example, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as, forexample, N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulphoxide, or alcohols such as methanol or ethanol.

Examples of oxidizing agents are halogenating agents such asN-chlorosuccinimide or hypervalent iodine compounds such asbis(acetato-O)phenyl iodide.

Step d)

The compounds of the formula (XXII) (corresponds to formula I(Q16) wherep=1) can be prepared anlogously to the process described inWO2015/002211 by reacting compounds of the formula (XXI) with anoxidizing agent.

Examples of a suitable oxidizing agent are sodium periodate andmeta-chloroperbenzoic acid.

Suitable solvents for the oxidation are, for example, halogenatedaliphatic hydrocarbons such as, for example, dichloromethane orchloroform, alcohols such as methanol or ethanol, and acetic acid.

Process E

The radicals R¹, R^(2a), R³, R¹¹, R¹², A¹, A², A⁴ and n have themeanings described above and X¹ represents halogen.

Step a)

The compounds of the formula (XXIII) can be prepared analogously toWO2015/002211 by reacting the compounds of the formula (VI) withcompounds of the formula (XVII).

Compounds of the formula (XVII) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (XXIII) (corresponds toformula I(Q10)) is generally carried out in a solvent. Preference isgiven to ethers such as, for example, tetrahydrofuran, methyl tert-butylether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbonssuch as hexane, heptane, aromatic hydrocarbons such as toluene, xylene,halogenated hydrocarbons such as, for example, dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene,aprotic polar solvents such as, for example, N,N-dimethylformamide,N-methylpyrrolidone, dimethyl sulphoxide, or esters such as, forexample, ethyl acetate, or nitriles such as acetonitrile.

The reaction can be carried out in the presence of a base. Examples ofsuitable bases are nitrogen heterocycles such as pyridine, picoline,2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary aminessuch as triethylamine and N,N-diisopropylethylamine; or inorganic basessuch as potassium phosphate, potassium carbonate and sodium hydride.

Process F

The radicals R¹, R^(2a), R³, R¹¹, R¹², A¹, A², A⁴ and n have themeanings described above and X¹ represents halogen.

Step a)

The compounds of the formula (XXV) (corresponds to formula I(Q11)) canbe prepared by reacting compounds of the formula (VI) with compounds ofthe formula (XXIV).

Compounds of the formula (XXIV) are either commercially available or canbe prepared by known methods.

The reaction proceeds under reaction conditions analogous to thosedescribed in process E.

Process G

The radicals R¹, R^(2a), R³, R¹¹, R¹³, A¹, A², A⁴ and n have themeanings described above and X¹ represents halogen.

The compounds of the formula (XXVII) (corresponds to formula I(Q15)) canbe prepared by reacting compounds of the formula (VI) with compounds ofthe formula (XXVI).

Compounds of the formula (XXVI) are either commercially available or canbe prepared by known methods.

The reaction proceeds under reaction conditions analogous to thosedescribed in process E.

Process H

The radicals R¹, R^(2a), R³, R¹¹, A¹, A², A⁴ and n have the meaningsdescribed above and X¹ represents halogen and Q represents O or S.

Step a)

The compounds of the formula (XXIX) can be prepared by reactingcompounds of the formula (VI) with compounds of the formula (XXVIII).

Compounds of the formula (XXVIII) are either commercially available orcan be prepared by known methods.

The reaction proceeds under reaction conditions analogous to thosedescribed in process E.

Step b)

The compounds of the formula (XXXII) (corresponds to formula I(Q12)where Q=O and I(Q13) where Q=S) can be prepared by reacting compounds ofthe formula (XXIX) with compounds of the formula (XXX).

Compounds of the formula (XXX) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (XXXII) is generally carriedout in a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, halogenated hydrocarbons such as, for example,dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene, aromatic hydrocarbons such as toluene, xylene, esterssuch as, for example, ethyl acetate, nitriles such as acetonitrile,aprotic polar solvents such as, for example, N,N-dimethylformamide,N-methylpyrrolidone, dimethyl sulphoxide or nitrogenous heterocyclessuch as pyridine or quinoline.

The reaction can be carried out in the presence of a condensing agent.Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and1,3-dicyclohexylcarbodiimide.

The reaction can be carried out in the presence of a suitable catalyst.An example of a suitable catalyst is 1-hydroxybenzotriazole.

The compounds of the formula (XXXII) can also be prepared by reactingcompounds of the formula (XXIX) with compounds of the formula (XXXI).

Compounds of the formula (XXXI) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (XXXII) is generally carriedout in a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatichydrocarbons such as toluene, xylene, halogenated hydrocarbons such as,for example, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as, forexample, N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulphoxide, or esters such as, for example, ethyl acetate, or nitrilessuch as acetonitrile.

The reaction can be carried out in the presence of a base. Examples ofsuitable bases are nitrogen heterocycles such as pyridine,dimethylaminopyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such astriethylamine and N,N-diisopropylethylamine; or inorganic bases such aspotassium carbonate and sodium hydride.

Process I

The radicals R¹, R², R³, R¹¹, R¹³, A¹, A², A⁴ and n have the meaningsdescribed above.

Step a)

The compounds of the formula (XXXIV) (corresponds to formula I(Q14)) canbe prepared by reacting compounds of the formula (XXIX) with compoundsof the formula (XXXIII).

Compounds of the formula (XXXIII) are either commercially available orcan be prepared by known methods.

The conversion to compounds of the formula (XXXIV) is generally carriedout in a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatichydrocarbons such as toluene, xylene, halogenated hydrocarbons such as,for example, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene, esters such as, for example, ethylacetate, nitriles such as acetonitrile or aprotic polar solvents suchas, for example, N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulphoxide.

The reaction can be carried out in the presence of a base. Examples ofsuitable bases are nitrogen heterocycles such as pyridine,dimethylaminopyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such astriethylamine and N,N-diisopropylethylamine; or inorganic bases such aspotassium carbonate and sodium hydride.

Process J

The radicals R¹, R^(2a), R³, A¹, A² and A⁴ have the meanings describedabove and X² represents halogen.

Step a)

The compounds of the formula (XXXVI) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with a carboxylic acid of the formula(XXXV) in the presence of a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (XXXV) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (XXXV) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure and at temperatures of 0 to 180° C.;with preference, the reaction is carried out at atmospheric pressure andtemperatures of 20 to 140° C.

Step b)

The compounds of the formula (XXXVII) can be prepared by condensing thecompounds of the formula (XXXVI), for example analogously to theprocesses described in WO2012/86848.

The conversion to compounds of the formula (XXXVII) can be effected neator in a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulphonic acids such as para-toluenesulphonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (XXXVIII) can be prepared by reacting thecompounds of the formula (XXXVII) with the compounds of the formula (X)in the presence of a base.

Mercaptan derivatives of the formula (X), for example methyl mercaptan,ethyl mercaptan or isopropyl mercaptan, are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in US2006/25633, US2006/111591, U.S. Pat. No.2,820,062, Chemical Communications, 13 (2000), 1163-1164 or Journal ofthe American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (XXXVIII) can be effectedneat or in a solvent, preference being given to conducting the reactionin a solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given to caesium carbonate, sodium carbonateand potassium carbonate. Further suitable bases are alkali metalhydrides, for example sodium hydride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step d)

The compounds of the formula (XXXIX) can be prepared by oxidizing thecompounds of the formula (XXXVIII). The oxidation is generally carriedout in a solvent selected from customary solvents which are inert underthe prevailing reaction conditions. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (XIXa) can be prepared by oxidizing thecompounds of the formula (XXXIX). The oxidation is generally carried outin a solvent. Preference is given to halogenated hydrocarbons, forexample dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol orethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

The further reaction of the compounds of the formulae (XIXa), (XXXVIII)and (XXXIX) is carried out analogously to processes D, H and I.

Process K

The radicals R¹, R^(2a), R³, R¹³, A¹, A², A⁴ and n have the meaningsdescribed above and X¹ represents halogen.

Step a)

The compounds of the formula (XXXXI) (corresponds to formula I(Q17)) canbe prepared by reacting compounds of the formula (VI) with compounds ofthe formula (XXXX), for example analogously to the process described inU.S. Pat. No. 4,558,134 or US2014/275026.

Compounds of the formula (XXXX) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (XXXXI) can be effected neator in a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate, potassium carbonate and potassium tert-butoxide. Furthersuitable bases are alkali metal hydrides, for example sodium hydride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Process L

The radicals R¹, R^(2a), R³, R¹³, A¹, A² and A⁴ have the meaningsdescribed above and X¹ represents halogen.

Step a)

The compounds of the formula (XXXXIII) (corresponds to formula I(Q5)where m=0) can be prepared by reacting compounds of the formula (XIII)with compounds of the formula (XXXXII).

Compounds of the formula (XXXXII) are either commercially available orcan be prepared by known methods.

The conversion to compounds of the formula (XXXXIII) can be effectedneat or in a solvent, preference being given to conducting the reactionin a solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulphoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate, potassium carbonate and potassium tert-butoxide. Furthersuitable bases are alkali metal hydrides, for example sodium hydride.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step b)

The compounds of the formula (XXXXIV) (corresponds to formula I(Q5)where m=1) can be prepared by oxidizing the compounds of the formula(XXXXIII). The oxidation is generally carried out in a solvent selectedfrom customary solvents which are inert under the prevailing reactionconditions. Preference is given to halogenated hydrocarbons, for exampledichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene; alcohols such as methanol or ethanol; formic acid, aceticacid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step c)

The compounds of the formula (XXXXV) (corresponds to formula I(Q5) wherem=2) can be prepared by oxidizing the compounds of the formula (XXXXIV).The oxidation is generally carried out in a solvent. Preference is givento halogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols suchas methanol or ethanol; formic acid, acetic acid, propionic acid orwater.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step d)

The compounds of the formula (XXXXV) can also be prepared in a one-stepprocess by oxidizing the compounds of the formula (XXXXIII). Theoxidation is generally carried out in a solvent. Preference is given tohalogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols suchas methanol or ethanol; formic acid, acetic acid, propionic acid orwater.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Process M

The radicals R¹, R^(2a), R³, R¹³, A¹, A² and A⁴ have the meaningsdescribed above. Ns=nosyl/4-nitrobenzylsulphonyl

Step a)

The compounds of the formula (XXXXVI) can be prepared by imination ofthe compounds of the formula (XXXXIV) with 4-nitrobenzylsulphonylamide(NsNH₂) and a hypervalent iodine compound with metal catalysis, forexample analogously to the processes described in Organic Letters 2006,8, 2349 und Chemistry—A European Journal 2007, 13, 6674.

The reaction of the compounds of the formula (XXXXVI) is preferablycarried out in a solvent selected from customary solvents which areinert under the prevailing reaction conditions. Preference is given tonitriles such as, for example, acetonitrile, or to halogenated alkanessuch as, for example, dichloromethane.

Examples of metal catalysts are iron, copper, silver or rhodiumcompounds, for example iron(II) acetylacetonate, iron(III)acetylacetonate and rhodium(II) acetate. Diacetoxyiodobenzene oriodosylbenzene are frequently used as hypervalent iodine compounds.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at room temperature.

Step b)

The compounds of the formula (XXXXVII) (corresponds to formula I(Q6))can be prepared from compounds of the formula (XXXXVI) by reaction witha thiol under basic conditions, for example analogously to the processesdescribed in Organic Letters 2006, 8, 2349; Chemistry—A European Journal2007, 13, 6674 and WO2006/101860.

The conversion to compounds of the formula (XXXXVII) is generallycarried out in a solvent.

Preference is given to ethers such as, for example, tetrahydrofuran, ornitriles such as acetonitrile.

The thiol used is, for example, thiophenol in combination with aninorganic base from the group consisting of carbonates of alkali oralkaline earth metals, for example caesium carbonate. The use of asolution of sodium thiomethoxide in methanol has also been described.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −78° C. to30° C.

Process N

The radicals R¹, R^(2a), R³, R¹³, A¹, A² and A⁴ have the meaningsdescribed above. Ns=nosyl/4-nitrobenzylsulphonyl.

Step a)

The compounds of the formula (XXXXVI) can be prepared by reactingcompounds of the formula (XXXXIII) analogously to the processesdescribed in process M, step a).

The further conversion of compounds of the formula (XXXXVI) to compoundsof the formula (XXXXVII) proceeds under reaction conditions analogous tothose described in process M.

Process O

The radicals R¹, R^(2a), R³, R¹³, A¹, A² and A⁴ have the meaningsdescribed above.

Step a)

The compounds of the formula (XXXXVIII) (corresponds to formula I(Q8))can be prepared from compounds of the formula (XXXXIII) by iminationwith cyanamide in the presence of a hypervalent iodine compound, forexample analogously to the processes described in Organic Letters 2007,9, 2951. The conversion to compounds of the formula (XXXXVIII) isgenerally carried out in acetonitrile as solvent. Diacetoxyiodobenzeneor iodosylbenzene are frequently used as hypervalent iodine compounds.The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to 30°C.

The compounds of the formula (XXXXVIII) can furthermore be prepared fromcompounds of the formula (XXXXIII) by imination with cyanamide in thepresence of N-bromosuccinimide (NBS) or iodine under basic conditions,for example analogously to the processes described in Organic Letters2007, 9, 3809 or WO2014/29830. In this case, the conversion to compoundsof the formula (XXXXVIII) is carried out in a solvent. Preference isgiven to using alcohols such as, for example, methanol, ethers such as,for example, tetrahydrofuran, or nitriles such as acetonitrile. Examplesof suitable bases are alkoxides such as, for example, potassiumtert-butoxide. Further suitable bases are alkali metal hydrides, forexample sodium hydride. The reaction can be carried out under reducedpressure, at atmospheric pressure or under elevated pressure, and atroom temperature.

Step b)

The compounds of the formula (XXXXIX) (corresponds to formula I(Q7)) canbe prepared from compounds of the formula (XXXXVIII) by oxidation underbasic conditions, for example analogously to the processes described inOrganic Letters 2007, 9, 2951; Organic Letters 2007, 9, 3809 orWO2014/140075. The oxidation is generally carried out in a solvent.Preference is given to alcohols such as ethanol. The oxidizing agentused is, for example, meta-chloroperbenzoic acid. Examples of suitablebases are carbonates such as, for example, potassium carbonate. Thereaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to 30°C.

Process P

The radicals R¹, R^(2a), R³, R¹¹, R¹², A¹, A² and A⁴ have the meaningsdescribed above. Bn=benzyl/CH₂Ph.

Step a)

The compounds of the formula (L) can be prepared from intermediates ofthe formula (XXXXIIIa) by oxidation in the presence of a chlorinesource, for example analogously to the processes described inWO2008/2244 and WO2010/24451.

The conversion to compounds of the formula (L) is generally carried outin a solvent. Preference is given to halogenated alkanes such as, forexample, dichloromethane or tetrachloromethane. Frequently, mixtureswith water are employed.

The chlorine sources and oxidizing agents used are, for example,chlorine gas, N-chlorosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin.

Frequently, the reactions are carried out in an acidic medium. Acidsused are, for example, carboxylic acids such as formic acid or aceticacid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of 0° C. to 30°C.

Step b)

The compounds of the formula (LII) (corresponds to formula I(Q9)) can beprepared from compounds of the formula (L) with compounds of the formula(XVII) under standard conditions.

The conversion to compounds of the formula (LII) is generally carriedout in a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatichydrocarbons such as toluene, xylene, halogenated hydrocarbons such as,for example, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene, esters such as, for example, ethylacetate, nitriles such as acetonitrile or aprotic polar solvents suchas, for example, N,N-dimethylformamide, N-methylpyrrolidone, dimethylsulphoxide.

The reaction can be carried out in the presence of a base. Examples ofsuitable bases are nitrogen heterocycles such as pyridine,dimethylaminopyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such astriethylamine and N,N-diisopropylethylamine; or inorganic bases such aspotassium carbonate and sodium hydride.

Process Q

The radicals R¹, R^(2a), R³, R⁸, A¹, A², A⁴ and n have the meaningsdescribed above, R¹¹ represents methyl, R¹² represents methoxy and Xrepresents halogen.

Step a)

The compounds of the formula (LIV) (corresponds to formula I(Q1)) can beprepared by conventing compounds of the formula (LIII) into anorganometallic compound and subsequent reaction with compounds of theformula (Ia), for example analogously to the processes described in U.S.Pat. No. 5,821,246 and European Journal of Medicinal Chemistry 2012, 58,p. 396.

Compounds of the formula (LIII) are either commercially available or canbe prepared by known methods.

The organometal compounds can be produced, for example, from compoundsof the formula (LIII) by reaction with magnesium or alkyllithiumcompounds.

The conversion to compounds of the formula (LV) is generally carried outin a solvent. Preference is given to ethers such as tetrahydrofuran ordiethyl ether.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −78° C. to45° C.

Step b)

Thioketones of the formula (LV) (corresponds to formula I(Q2)) can beprepared from compounds of the formula (LIV) by reaction with asulphurizing agent, for example Lawesson's reagent or P₄S₁₀.

Process R

The radicals R¹, R^(2a), R³, R⁸, R¹¹, R¹², A¹, A², A⁴ and n have themeanings described above and X¹ represents halogen.

Compounds of the formula (LVI) can be prepared, for example, fromcompounds of the formula (VI) in which X¹ preferably represents halogenfrom the group consisting of chlorine or bromine, by generally knownmethods (cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58,9633-9695; Metal-Catalyzed Cross-Coupling Reactions (eds.: A. deMeijere, F. Diederich), 2^(nd) ed., Wiley-VCH, Weinheim, 2004).

For example, compounds of the formula (VI) can be reacted with suitableolefinic boronic acids or esters thereof by known methods (cf.WO2006/21805) in the presence of suitable catalysts from the group ofthe transition metal salts to give compounds of the formula (LVI).Examples of preferred coupling catalysts include palladium catalystssuch as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) ortetrakis(triphenylphosphine)palladium. Suitable basic reactionauxiliaries used to conduct the processes are preferably carbonates ofsodium or potassium.

Some of the olefinic boronic acids or olefinic boronic esters requiredare known and/or commercially available, or they can be prepared bygenerally known methods (cf. Boronic Acids (eds.: D. G. Hall), 2^(nd)ed., Wiley-VCH, Weinheim, 2011).

The invention also provides compounds of the formula (IX)

in whichR^(2a), R³, A¹, A² and A⁴ have the meanings described above and X¹ andX² represent halogen (preferably fluorine, chlorine, bromine, iodine,particularly preferably chlorine or fluorine).

Preference is given to compounds of the formula (IX) in which A¹represents nitrogen, A² represents N-methyl, A⁴ represents CH, X¹represents halogen, X² represents halogen and

R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

Particular preference is given to compounds of the formula (IX) in whichA¹ represents nitrogen, A² represents N-methyl, A⁴ represents CH, X¹represents chlorine or fluorine, X² represents chlorine or fluorine and

R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

The invention also provides compounds of the formula (XI)

in whichR¹, R^(2a), R³, A¹, A² and A⁴ have the meanings described above and X¹represents halogen (preferably fluorine, chlorine, bromine, iodine,particularly preferably chlorine or fluorine).

Preference is given to compounds of the formula (XI) in which A¹represents nitrogen, A² represents N-methyl, A⁴ represents CH, X¹represents halogen and

R¹, R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

Particular preference is given to compounds of the formula (XI) in whichA¹ represents nitrogen, A² represents N-methyl, A⁴ represents CH, X¹represents chlorine or fluorine and

R¹, R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

The invention also provides compounds of the formula (XII)

in whichR¹, R^(2a), R³, A¹, A² and A⁴ have the meanings described above and X¹represents halogen (preferably fluorine, chlorine, bromine, iodine,particularly preferably chlorine or fluorine).

Preference is given to compounds of the formula (XII) in which A¹represents nitrogen, A² represents N-methyl, A⁴ represents CH, X¹represents halogen and

R¹, R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

Particular preference is given to compounds of the formula (XII) inwhich A¹ represents nitrogen, A² represents N-methyl, A⁴ represents CH,X¹ represents chlorine or fluorine and

R¹, R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

The invention also provides compounds of the formula (XIII)

in whichR¹, R^(2a), R³, A¹, A² and A⁴ have the meanings described above and X¹represents halogen (preferably fluorine, chlorine, bromine, iodine,particularly preferably chlorine or fluorine).

Preference is given to compounds of the formula (XIII) in which A¹represents nitrogen, A² represents N-methyl, A⁴ represents CH, X¹represents halogen and

R¹, R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).

Particular preference is given to compounds of the formula (XIII) inwhich A¹ represents nitrogen, A² represents N-methyl, A⁴ represents CH,X¹ represents chlorine or fluorine and

R¹, R^(2a) and R³ have the meanings described in configuration (1) orconfiguration (1-1) or configuration (1-2) or configuration (2) orconfiguration (2-1) or configuration (2-2) or configuration (3) orconfiguration (3-1) or configuration (3-2) or configuration (4) orconfiguration (4-1) or configuration (4-2) or configuration (5-2a) orconfiguration (5-2b).Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablycarried out in agriculture and forestry, and in material protection.Preferably excluded from this are methods for the surgical ortherapeutic treatment of the human or animal body and diagnostic methodscarried out on the human or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection agents.

In the context of the present application, the term “pesticide” alsoalways comprises the term “crop protection agent”.

The compounds of the formula (I), given good plant tolerance, favourablehomeotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, nematodes and molluscs, which are encountered inagriculture, in horticulture, in animal husbandry, in aquatic cultures,in forests, in gardens and leisure facilities, in the protection ofstored products and of materials, and in the hygiene sector. They canpreferably be used as pesticides. They are active against normallysensitive and resistant species and also against all or some stages ofdevelopment. The abovementioned pests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coniferarum, Oligonychusilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychuspratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp.,Ornithonyssus spp., Panonychus spp., for example Panonychus citri(=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., for example Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., for example Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici; from the class of the Chilopoda, for example Geophilusspp., Scutigera spp.;from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;from the class of the Diplopoda, for example Blaniulus guttulatus;from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., forexample Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agriotes spp., for example Agriotes linneatus, Agriotes mancus,Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum,Anoplophora spp., Anthonomus spp., for example Anthonomus grandis,Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., for exampleAtomaria linearis, Attagenus spp., Baris caerulescens, Bruchidiusobtectus, Bruchus spp., for example Bruchus pisorum, Bruchus rufimanus,Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., for exampleCeutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchusrapae, Chaetocnema spp., for example Chaetocnema confinis, Chaetocnemadenticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp.,Cosmopolites spp., for example Cosmopolites sordidus, Costelytrazealandica, Ctenicera spp., Curculio spp., for example Curculio caryae,Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestesferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp.,for example Diabrotica balteata, Diabrotica barberi, Diabroticaundecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata,Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocisspp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachnaspp., for example Epilachna borealis, Epilachna varivestis, Epitrixspp., for example Epitrix cucumeris, Epitrix fuscula, Epitrixhirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.,Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hyperapostica, Hypomeces squamosus, Hypothenemus spp., for exampleHypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae,Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp.,for example Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus(=Hyperodes) spp., Lixus spp., Luperomorpha xanthodera, Luperodes spp.,Lyctus spp., Megascelis spp., Melanotus spp., for example Melanotuslongulus oregonensis, Meligethes aeneus, Melolontha spp., for exampleMelolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., for example Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., Oulema oryzae, Oxycetonia jucunda,Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotretaspp., for example Phyllotreta armoraciae, Phyllotreta pusilla,Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica,Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., for examplePsylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata,Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorusspp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylonperforans, Sitophilus spp., for example Sitophilus granarius, Sitophiluslinearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp.,Stegobium paniceum, Stemechus spp., for example Stemechus paludatus,Symphyletes spp., Tanymecus spp., for example Tanymecus dilaticollis,Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioidesmauretanicus, Tribolium spp., for example Tribolium audax, Triboliumcastaneum, Tribolium confusum, Trogoderma spp., Tychius spp.,Xylotrechus spp., Zabrus spp., for example Zabrus tenebrioides;from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleiaheraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopotaspp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp.,Hypoderma spp., Liriomyza spp., for example Liriomyza brassicae,Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., for exampleLucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., for exampleMusca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit,Paratanytarsus spp., Paralauterbomiella subcincta, Pegomya spp., forexample Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomusspp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., forexample Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta,Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex, Toxotrypana curvicauda;from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., for example Amrasca bigutulla, Amrasca devastans, Anuraphiscardui, Aonidiella spp., for example Aonidiella aurantii, Aonidiellacitrina, Aonidiella inomata, Aphanostigma piri, Aphis spp., for exampleAphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphisglycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphismiddletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola,Aphis vibumiphila, Arboridia apicalis, Arytainilla spp., Aspidiellaspp., Aspidiotus spp., for example Aspidiotus nerii, Atanus spp.,Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis,Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp.,Brevicoryne brassicae, Cacopsylla spp., for example Cacopsylla pyricola,Calligypona marginata, Capulinia spp., Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea,Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus,Cicadulina mbila, Coccomytilus halli, Coccus spp., for example Coccushesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis,Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp.,Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspisspp., Diuraphis spp., Drosicha spp., Dysaphis spp., for example Dysaphisapiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp.,Empoasca spp., for example Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., for exampleEriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspisspp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodiscacoagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., forexample Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., for example Lecanium corni(=Parthenolecanium comi), Lepidosaphes spp., for example Lepidosaphesulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula,Macrosiphum spp., for example Macrosiphum euphorbiae, Macrosiphum lilii,Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphissacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum,Monellia costalis, Monelliopsis pecanis, Myzus spp., for example Myzusascalonicus, Myzus cerasi, Myzus ligustri, Myzus omatus, Myzus persicae,Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettixspp., for example Nephotettix cincticeps, Nephotettix nigropictus,Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Ortheziapraelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae,Paratrioza spp., for example Paratrioza cockerelli, Parlatoria spp.,Pemphigus spp., for example Pemphigus bursarius, Pemphigus populivenae,Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., for examplePhenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli,Phylloxera spp., for example Phylloxera devastatrix, Phylloxeranotabilis, Pinnaspis aspidistrae, Planococcus spp., for examplePlanococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., for example Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psyllaspp., for example Psylla buxi, Psylla mali, Psylla pyri, Pteromalusspp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., for exampleQuadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus pemiciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., for example Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., for example Saissetia coffeae, Saissetia miranda, Saissetianeglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum,Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., for example Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., for example Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., for example Cimexadjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus,Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus,Diconocoris hewetti, Dysdercus spp., Euschistus spp., for exampleEuschistus heros, Euschistus servus, Euschistus tristigmus, Euschistusvariolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys,Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisavaricornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocorisspp., for example Lygocoris pabulinus, Lygus spp., for example Lyguselisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacoptacribraria, Miridae, Monalonion atratum, Nezara spp., for example Nezaraviridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata,Piezodorus spp., for example Piezodorus guildinii, Psallus spp.,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.;from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Camponotus spp.,Dolichovespula spp., Diprion spp., for example Diprion similis,Hoplocampa spp., for example Hoplocampa cookei, Hoplocampa testudinea,Lasius spp., Linepithema humile, Monomorium pharaonis, Paratrechinaspp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsisinvicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp.,for example Vespa crabro, Wasmannia auropunctata, Xeris spp.;from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber; from the order of the Isoptera, forexample Coptotermes spp., for example Coptotermes formosanus, Comitermescumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp.,Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermesspp., Reticulitermes spp., for example Reticulitermes flavipes,Reticulitermes hesperus;from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra,Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseolaspp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsapomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., forexample Chilo plejadellus, Chilo suppressalis, Choreutis pariana,Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolophaaurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp.,for example Ephestia elutella, Ephestia kuehniella, Epinotia spp.,Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiellaspp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp.,for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleriamellonella, Gracillaria spp., Grapholitha spp., for example Grapholitamolesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., forexample Helicoverpa armigera, Helicoverpa zea, Heliothis spp., forexample Heliothis virescens, Hofmannophila pseudospretella, Homoeosomaspp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata,Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis,Leucoptera spp., for example Leucoptera coffeella, Lithocolletis spp.,for example Lithocolletis blancardella, Lithophane antennata, Lobesiaspp., for example Lobesia botrana, Loxagrotis albicosta, Lymantria spp.,for example Lymantria dispar, Lyonetia spp., for example Lyonetiaclerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae,Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata,Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp.,Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., for exampleOstrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea,Parnara spp., Pectinophora spp., for example Pectinophora gossypiella,Perileucoptera spp., Phthorimaea spp., for example Phthorimaeaoperculella, Phyllocnistis citrella, Phyllonorycter spp., for examplePhyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp.,for example Pieris rapae, Platynota stultana, Plodia interpunctella,Plusia spp., Plutella xylostella (=Plutella maculipennis), Prays spp.,Prodenia spp., Protoparce spp., Pseudaletia spp., for examplePseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis,Rachiplusia nu, Schoenobius spp., for example Schoenobius bipunctifer,Scirpophaga spp., for example Scirpophaga innotata, Scotia segetum,Sesamia spp., for example Sesamia inferens, Sparganothis spp.,Spodoptera spp., for example Spodoptera eradiana, Spodoptera exigua,Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenomaspp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tineapellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,Trichoplusia spp., for example Trichoplusia ni, Tryporyza incertulas,Tuta absoluta, Virachola spp.;from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., for example Frankliniellafusca, Frankliniella occidentalis, Frankliniella schultzei,Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi,Haplothrips spp., Heliothrips spp., Hercinothrips femoralis,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi,Thrips spp., for example Thrips palmi, Thrips tabaci;from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata;pests from the phylum of the Mollusca, in particular from the class ofthe Bivalvia, for example Dreissena spp.;and also from the class of the Gastropoda, for example Arion spp., forexample Arion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;animal and human parasites from the phyla of the Platyhelminthes andNematoda, for example Aelurostrongylus spp., Amidostomum spp.,Ancylostoma spp., Angiostrongylus spp., Anisakis spp., Anoplocephalaspp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp.,Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp.,Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp.,Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilariaspp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobiusspp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsisspp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronemaspp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepisspp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylusspp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muelleriusspp., Necator spp., Nematodirus spp., Nippostrongylus spp.,Oesophagostomum spp., Ollulanus spp., Onchocerca spp., Opisthorchisspp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp.,Parafilaria spp., Paragonimus spp., Paramphistomum spp.,Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylusspp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilariaspp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamusspp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp.,Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylusspp., Trichuris spp., Uncinaria spp., Wuchereria spp.;plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, especially Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorusspp., for example Longidorus africanus, Meloidogyne spp., for exampleMeloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla,Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp.,Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., forexample Paratrichodorus minor, Pratylenchus spp., for examplePratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp.,Punctodera spp., Quinisulcius spp., Radopholus spp., for exampleRadopholus citrophilus, Radopholus similis, Rotylenchulus spp.,Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp.,for example Trichodorus obtusus, Trichodorus primitivus, Tylenchulusspp., Tylenchorhynchus spp., for example Tylenchorhynchus annulatus,Tylenchulus spp., for example Tylenchulus semipenetrans, Xiphinema spp.,for example Xiphinema index.

In addition, it is possible to control, from the sub-kingdom of theProtozoa, the order of the Coccidia, for example Eimeria spp.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). If appropriate, they can also be used as intermediates orprecursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I). In somecases, the use forms comprise further pesticides and/or adjuvants whichimprove action, such as penetrants, e.g. vegetable oils, for examplerapeseed oil, sunflower oil, mineral oils, for example paraffin oils,alkyl esters of vegetable fatty acids, for example rapeseed oil methylester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders,for example alkylsiloxanes and/or salts, for example organic orinorganic ammonium or phosphonium salts, for example ammonium sulphateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulphosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemically active compounds.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries such as, for example,extenders, solvents and/or solid carriers and/or other auxiliaries suchas, for example, surfactants. The formulations are produced either insuitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and water.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, suchas chlorobenzene, chloroethylene or methylene chloride, aliphatichydrocarbons, such as cyclohexane, paraffins, mineral oil fractions,mineral and vegetable oils, alcohols, such as methanol, ethanol,isopropanol, butanol or glycol and their ethers and esters, ketones suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, andalso water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as finely divided silica, alumina and natural orsynthetic silicates, resins, waxes and/or solid fertilizers. It islikewise possible to use mixtures of such carriers. Useful carriers forgranules include: for example crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite, dolomite, and syntheticgranules of inorganic and organic flours, and also granules of organicmaterial such as sawdust, paper, coconut shells, corn cobs and tobaccostalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable are those extenders or carriers which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulphonic acid, salts of phenolsulphonic acid ornaphthalenesulphonic acid, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, with substitutedphenols (preferably alkylphenols or arylphenols), salts ofsulphosuccinic esters, taurine derivatives (preferably alkyl taurates),phosphoric esters of polyethoxylated alcohols or phenols, fatty acidesters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is advantageous if one of the compounds of theformula (I) and/or one of the inert carriers is insoluble in water andwhen the application takes place in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom are dyes such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients andtrace nutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers,preservatives, antioxidants, light stabilizers, or other agents whichimprove chemical and/or physical stability. Foam generators or antifoamsmay also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) can be combinedwith any solid or liquid additive commonly used for formulationpurposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulphosuccinate, orincrease viscoelasticity, for example hydroxypropylguar polymers.

Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of agrochemicalactive compounds into plants. Penetrants are defined in this context bytheir ability to penetrate from the (generally aqueous) applicationliquor and/or from the spray coating into the cuticle of the plant andhence increase the mobility of the active compounds in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), more preferably between 0.01%and 95% by weight of the compound of the formula (I), most preferablybetween 0.5% and 90% by weight of the compound of the formula (I), basedon the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active compound combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessability of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used in mixtures with agents to improve plant properties, forexample growth, yield and quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case.

Insecticides/Acaricides/Nematicides

The active compounds specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example,carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion,parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon,phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos,pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfonand vamidothion.(2) GABA-gated chloride channel antagonists, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.(3) Sodium channel modulators/voltage-gated sodium channel blockers, forexample pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin,d-trans allethrin, bifenthrin, bioallethrin, bioallethrins-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin,empenthrin [(EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox,imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin[(1R)-trans isomer], prallethrin, pyrethrins (pyrethrum), resmethrin,silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer)],tralomethrin and transfluthrin or DDT or methoxychlor.(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for exampleneonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.(5) Allosteric activators of the nicotinergic acetylcholine receptor(nAChR), for example spinosyns, e.g. spinetoram and spinosad.(6) Chloride channel activators, for example avermectins/milbemycins,e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.(7) Juvenile hormone imitators, for example, juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.(8) Active compounds having unknown or nonspecific mechanisms of action,for examplealkyl halides, e.g. methyl bromide and other alkyl halides; orchloropicrine or sulphuryl fluoride or borax or tartar emetic.(9) Selective antifeedants, e.g. pymetrozine or flonicamid.(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox anddiflovidazin or etoxazole.(11) Microbial disruptors of the insect gut membrane, e.g. Bacillusthuringiensis subspecies israelensis, Bacillus sphaericus, Bacillusthuringiensis subspecies aizawai, Bacillus thuringiensis subspecieskurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plantproteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,Cry34/35Ab1.(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatin andfenbutatin oxide or propargite or tetradifon.(13) Oxidative phosphorylation decouplers that interrupt the H protongradient, for example chlorfenapyr, DNOC and sulfluramid.(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.(15) Chitin biosynthesis inhibitors, type 0, for example bistrifluron,chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron andtriflumuron.(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin.(17) Moulting inhibitors (especially for Diptera, i.e. dipterans), forexample cyromazine.(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.(19) Octopaminergic agonists, for example amitraz.(20) Complex-III electron transport inhibitors, for examplehydramethylnon or acequinocyl or fluacrypyrim.(21) Complex-I electron transport inhibitors, for example METIacaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.(24) Complex-IV electron transport inhibitors, for example phosphines,e.g. aluminium phosphide, calcium phosphide, phosphine and zincphosphide or cyanide.(25) Complex-II electron transport inhibitors, for example cyenopyrafenand cyflumetofen.(28) Ryanodine receptor effectors, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide.

Further active compounds having an unknown or unclear mechanism ofaction, for example afidopyropen, afoxolaner, azadirachtin, benclothiaz,benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat,cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz,dicofol, diflovidazin, flometoquin, fluazaindolizine, fluensulfone,flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram,fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin,imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding,pyflubumide, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, triflumezopyrim and iodomethane; and additionallypreparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and thefollowing known active compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanon(known from WO2003/106457),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known fromWO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbony1}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (knownfrom WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from CN102057925),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2009/080250),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672),1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),4-(3-({2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN101337940),N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO2008/134969), butyl[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]carbonate(known from CN 102060818),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridinylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213,N-(methylsulphonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboxamide(known from WO2012/000896),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926).

Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” or on the Internet (forexample: http://www.alanwood.net/pesticides).

All the fungicidal mixing components listed in classes (1) to (15) mayoptionally form salts with corresponding bases or acids if suitablefunctional groups are present. In addition, the fungicidal mixingcomponents listed in classes (1) to (15) also include tautomeric formsif tautomerism is possible.

(1) Ergosterol biosynthesis inhibitors, for example (1.01) aldimorph,(1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05)cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08)diniconazole, (1.09) diniconazole-M, (1.10) dodemorph, (1.11) dodemorphacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol,(1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18)fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21)flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24)furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalilsulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole,(1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole,(1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44)quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47)tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50)triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole,(1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57)uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,(1.62)N′-({5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideand (1.64) O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole1-carbothioate, (1.65) pyrisoxazole, (1.66)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.67)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.68)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.69)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.70)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.71)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.72)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.73)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.74)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.75)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.76)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.77)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.78)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.79)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.80)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.81)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.82)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.83)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.84)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.85)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.86)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.87)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.88)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.89)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triaz-1-yl)butan-2-ol,(1.90)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.91)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.92)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.93)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.94)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.95)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol.2) Inhibitors of the respiratory chain at complex I or II, for example(2.01) bixafen, (2.02) boscalid, (2.03) carboxin, (2.04) diflumetorim,(2.05) fenfuram, (2.06) fluopyram, (2.07) flutolanil, (2.08)fluxapyroxad, (2.09) furametpyr, (2.10) furmecyclox, (2.11) isopyrazam(mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate1RS,4SR,9SR), (2.12) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR),(2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18)mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad,(2.22) sedaxan, (2.23) thifluzamid, (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluorethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine,(2.29) benzovindiflupyr, (2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.32)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.35)1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.36)1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.37)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.38)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.39)1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(2.43) isofetamid, (2.44)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.45)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.46)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.47)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.48)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.49)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.50)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.51) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (2.52)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.53)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.54)3-(difluoromethyl)-N-(4′-ethinylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.55)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.56) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (2.57)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(2.58)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(2.59)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.60)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(2.61)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.62)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(2.63)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(2.64)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.65)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.66)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.67)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorphenyl)propan-2-yl]-1H-pyrazole-4-carboxamide,(2.68)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.69)3-(difluoromethyl)-N-[(3R)-7-fluoro1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.70)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide.3) Inhibitors of the respiratory chain at complex III, for example(3.01) ametoctradin, (3.02) amisulbrom, (3.03) azoxystrobin, (3.04)cyazofamid, (3.05) coumethoxystrobin, (3.06) coumoxystrobin, (3.07)dimoxystrobin, (3.08) enoxastrobin, (3.09) famoxadone, (3.10)fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13)kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16)picoxystrobin, (3.17) pyraclostrobin, (3.18) pyrametostrobin, (3.19)pyraoxystrobin, (3.20) pyribencarb, (3.21) triclopyricarb, (3.22)trifloxystrobin, (3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,(3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetamide,(3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide,(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.27) fenaminostrobin, (3.28)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.29) methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanyl)methyl]phenyl}-3-methoxyacrylate,(3.30)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.31)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.33)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide.4) Inhibitors of mitosis and cell division, for example (4.01) benomyl,(4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05)ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron,(4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate,(4.12) zoxamide, (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,(4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.5) Compounds capable of having multisite action, for example (5.01)Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04) chlorothalonil,(5.05) copper hydroxide, (5.06) copper naphthenate, (5.07) copper oxide,(5.08) copper oxychloride, (5.09) copper(2+) sulphate, (5.10)dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13) dodine free base,(5.14) ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine,(5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadinealbesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23)mancozeb, (5.24) maneb, (5.25) metiram, (5.26) metiram zinc, (5.27)oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulphur andsulphur preparations including calcium polysulphide, (5.31) thiram,(5.32) tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine.6) Compounds capable of inducing host defence, for example (6.01)acibenzolar-S-methyl, (6.02) isotianil, (6.03) probenazole, (6.04)tiadinil, (6.05) laminarin.7) Inhibitors of the amino acid and/or protein biosynthesis, for example(7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04)kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06)mepanipyrim, (7.07) pyrimethanil, (7.08)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(7.09) oxytetracycline, (7.10) streptomycin.8) Inhibitors of ATP production, for example (8.01) fentin acetate,(8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.9) Inhibitors of cell wall synthesis, for example (9.01)benthiavalicarb, (9.02) dimethomorph, (9.03) flumorph, (9.04)iprovalicarb, (9.05) mandipropamid, (9.06) polyoxins, (9.07) polyoxorim,(9.08) validamycin A, (9.09) valifenalate, (9.10) polyoxin B, (9.11)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.12)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.10) Inhibitors of lipid and membrane synthesis, for example (10.01)biphenyl, (10.02) chloroneb, (10.03) dicloran, (10.04) edifenphos,(10.05) etridiazole, (10.06) iodocarb, (10.07) iprobenfos, (10.08)isoprothiolane, (10.09) propamocarb, (10.10) propamocarb hydrochloride,(10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14)tecnazene, (10.15) tolclofos-methyl.11) Inhibitors of melanin biosynthesis, for example (11.01) carpropamid,(11.02) diclocymet, (11.03) fenoxanil, (11.04) phthalide, (11.05)pyroquilon, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.12) Inhibitors of nucleic acid synthesis, for example (12.01) benalaxyl,(12.02) benalaxyl-M (kiralaxyl), (12.03) bupirimate, (12.04) clozylacon,(12.05) dimethirimol, (12.06) ethirimol, (12.07) furalaxyl, (12.08)hymexazole, (12.09) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11)ofurace, (12.12) oxadixyl, (12.13) oxolinic acid, (12.14) octhilinone.13) Inhibitors of signal transduction, for example (13.01) chlozolinate,(13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05)procymidone, (13.06) quinoxyfen, (13.07) vinclozolin, (13.08)proquinazid.14) Compounds capable of acting as uncouplers, for example (14.01)binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04) fluazinam,(14.05) meptyldinocap.15) Further compounds, for example (15.001) benthiazole, (15.002)bethoxazin, (15.003) capsimycin, (15.004) carvone, (15.005)chinomethionat, (15.006) pyriofenone (chlazafenone), (15.007) cufraneb,(15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide,(15.011) dazomet, (15.012) debacarb, (15.013) dichlorophen, (15.014)diclomezine, (15.015) difenzoquat, (15.016) difenzoquat metilsulphate,(15.017) diphenylamine, (15.018) ecomate, (15.019) fenpyrazamine,(15.020) flumetover, (15.021) fluoroimide, (15.022) flusulfamide,(15.023) flutianil, (15.024) fosetyl-aluminium, (15.025)fosetyl-calcium, (15.026) fosetyl-sodium, (15.027) hexachlorobenzene,(15.028) irumamycin, (15.029) methasulfocarb, (15.030) methylisothiocyanate, (15.031) metrafenone, (15.032) mildiomycin, (15.033)natamycin, (15.034) nickel dimethyldithiocarbamate, (15.035)nitrothal-isopropyl, (15.036) oxamocarb, (15.037) oxyfenthiin, (15.038)pentachlorophenol and salts, (15.039) phenothrin, (15.040) phosphorousacid and it salts, (15.041) propamocarb-fosetylate, (15.042)propanosin-sodium, (15.043) pyrimorph, (15.044) pyrrolnitrin, (15.045)tebufloquin, (15.046) tecloftalam, (15.047) tolnifanide, (15.048)triazoxide, (15.049) trichlamide, (15.050) zarilamid, (15.051)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (15.052)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.053)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.054) oxathiapiproline, (15.055)1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate,(15.056) 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.057)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.058)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.059)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.060)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.061)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(15.062) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.063)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.064) 2-phenylphenol and salts, (15.065)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.066) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.067)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.068)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.069) 5-amino-1,3,4-thiadiazole-2-thiol, (15.070)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,(15.071) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.072)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.073)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.074) ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (15.075)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.076)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.077)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.078)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(15.079)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(15.080)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(15.081)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.082)N—{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.083)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.084)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acety}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,(15.085)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.086)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.087) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.088) phenazine-1-carboxylic acid, (15.089) quinolin-8-ol, (15.090)quinolin-8-ol sulphate (2:1), (15.091) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.092)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(15.093)N-[2-(4-{([3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide,(15.094) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.095)but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.096) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.097) propyl3,4,5-trihydroxybenzoate, (15.098)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.099)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.100)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.101)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(15.102) 2-(6-benzylpyridin-2-yl)quinazoline, (15.103)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.104)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.105) abscisic acid, (15.106)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(15.107)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.108)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.109)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.110)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (15.111)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.112)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.113)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.114)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.115)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.116)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.117)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.118)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.119)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.120)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.121)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.122)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.123)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.124)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.125)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.126)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.127)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(15.128)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.129)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.130)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.131)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(15.132)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(15.133)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(15.134)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.135)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.136)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.137)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.138)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.139)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.140)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.141)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.142)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.143)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.144)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.145)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.146)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.147)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.148)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.149)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine,(15.150)N′-(4-{3-[(difluoromethyl)sulphanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.151)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.152)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.153)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.154)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulphanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(15.155)N′-(4-{[3-(difluoromethoxy)phenyl]sulphanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.156)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.157)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.158)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.159)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulphanyl}phenyl)-N-ethyl-N-methylimidoformamide,(15.160)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.161)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.162)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.163)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulphonate, (15.164)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.165)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.166)2-[3,5-bis(difluoromethyl)-1H-pyrazol-11-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.167)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.168)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.169)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.170)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.171)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulphonate, (15.172)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulphonate, (15.173)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.174)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate.Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides include especially bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM 1-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421) Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii, (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (AccessionNumber CNCM 1-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Exampleswhich may be mentioned are:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugarbeet, sugar cane, tomatoes, peas and other types of vegetable, cotton,tobacco, oilseed rape, and also fruit plants (with the fruits apples,pears, citrus fruits and grapevines). Crop plants may be plants whichcan be obtained by conventional breeding and optimization methods or bybiotechnological and genetic engineering methods or combinations ofthese methods, including the transgenic plants and including the plantcultivars which are protectable or non-protectable by plant breeders'rights. Plant parts shall be understood to mean all parts and organs ofthe plants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested material and vegetative and generativepropagation material, for example cuttings, tubers, rhizomes, slips andseeds.

Treatment according to the invention of the plants and plant parts withthe compounds of the formula (I) is carried out directly or by allowingthe compounds to act on their surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and partsthereof in accordance with the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding methods, such as crossing or protoplastfusion, and parts thereof, are treated. In a further preferredembodiment, transgenic plants and plant cultivars obtained by geneticengineering methods, if appropriate in combination with conventionalmethods (genetically modified organisms), and parts thereof are treated.The term “parts” or “parts of plants” or “plant parts” has beenexplained above. Particular preference is given in accordance with theinvention to treating plants of the respective commercially customaryplant cultivars or those that are in use. Plant cultivars are understoodto mean plants having new properties (“traits”) and which have beengrown by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better storage life and/or processability of theharvested products. Further and particularly emphasized examples of suchproperties are increased resistance of the plants against animal andmicrobial pests, such as insects, arachnids, nematodes, mites, slugs andsnails owing, for example, to toxins formed in the plants, in particularthose produced in the plants by the genetic material from Bacillusthuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c),CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and alsocombinations thereof), and also increased resistance of the plantsagainst phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosates or phosphinothricin (for example the “PAT”gene). The genes which impart the desired properties (“traits”) inquestion may also be present in combinations with one another in thetransgenic plants. Examples of transgenic plants include the importantcrop plants, such as cereals (wheat, rice, triticale, barley, rye,oats), maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes,peas and other types of vegetable, cotton, tobacco, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapevines), particular emphasis being given to maize, soya beans,wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseed rape.Properties (“traits”) which are particularly emphasized are theincreased resistance of the plants to insects, arachnids, nematodes andslugs and snails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) directly or by action on their surroundings, habitat or storagespace using customary treatment methods, for example by dipping,spraying, atomizing, irrigating, evaporating, dusting, fogging,broadcasting, foaming, painting, spreading-on, injecting, watering(drenching), drip irrigating and, in the case of propagation material,in particular in the case of seed, additionally by dry seed treatment,liquid seed treatment, slurry treatment, by incrusting, by coating withone or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.compounds of the formula (I) are applied to the foliage, where treatmentfrequency and the application rate should be adjusted according to thelevel of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I) areintroduced in solid form (e.g. in the form of granules) into the locusof the plants. In the case of paddy rice crops, this can also beaccomplished by metering the compound of the formula (I) in a solidapplication form (for example as granules) into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements. However,the treatment of seed entails a series of problems which cannot alwaysbe solved in a satisfactory manner. Thus, it is desirable to developmethods for protecting the seed and the germinating plant which dispensewith, or at least reduce considerably, the additional application ofpesticides during storage, after sowing or after emergence of theplants. It is additionally desirable to optimize the amount of activecompound used so as to provide optimum protection for the seed and thegerminating plant from attack by animal pests, but without damage to theplant itself by the active compound used. In particular, methods for thetreatment of seed should also take account of the intrinsic insecticidalor nematicidal properties of pest-resistant or -tolerant transgenicplants in order to achieve optimal protection of the seed and thegerminating plant with a minimum expenditure of pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants, from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It also comprises amethod where the seed is treated at different times with a compound ofthe formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) for protection from animal pests. Theinvention also relates to seed which has been treated simultaneouslywith a compound of the formula (I) and a mixing component. The inventionfurther relates to seed which has been treated at different times with acompound of the formula (I) and a mixing component. In the case of seedwhich has been treated at different times with a compound of the formula(I) and a mixing component, the individual substances may be present onthe seed in different layers. In this case, the layers comprising acompound of the formula (I) and a mixing component may optionally beseparated by an intermediate layer. The invention also relates to seedin which a compound of the formula (I) and mixing component have beenapplied as part of a coating or as a further layer or further layers inaddition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages encountered with a systemically acting compound ofthe formula (I) is the fact that, by treating the seed, not only theseed itself but also the plants resulting therefrom are, afteremergence, protected against animal pests. In this way, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in greenhouses, inforests or in horticulture. More particularly, this includes seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beet (for example sugar beet and fodder beet), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for the treatment of transgenic seed containing atleast one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. Thus, for example, it is possible to use seed whichhas been harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been imbibed in water up to a certainstage (pigeon breast stage) for example, which leads to improvedgermination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed ina suitable formulation. Suitable formulations and processes for seedtreatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are produced in a known manner, by mixing compoundsof the formula (I) with customary additives, for example customaryextenders and solvents or diluents, dyes, wetters, dispersants,emulsifiers, antifoams, preservatives, secondary thickeners, stickers,gibberellins and also water.

Colorants which may be present in the seed-dressing formulations usablein accordance with the invention are all colorants which are customaryfor such purposes. It is possible to use either pigments, which aresparingly soluble in water, or dyes, which are soluble in water.Examples include the dyes known by the names Rhodamine B, C.I. PigmentRed 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical compounds. Preference is given to using alkylnaphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical compounds. Preference is given tousing nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Suitable nonionic dispersants include in particularethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants areespecially lignosulphonates, polyacrylic acid salts andarylsulphonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalcompounds. Silicone antifoams and magnesium stearate can be used withpreference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful adhesives which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schadlingsbekaimpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or use forms prepared therefrom, allmixing units usable customarily for the seed dressing are useful.Specifically, the procedure in seed dressing is to place the seed into amixer in batchwise or continuous operation, to add the particulardesired amount of seed dressing formulations, either as such or afterprior dilution with water, and to mix until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasites”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects and acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable homeotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer,and particularly cattle and pigs; poultry such as turkeys, ducks, geese,and particularly chickens; fish and crustaceans, for example inaquaculture, and also insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds, reptiles, amphibians and aquarium fish.

In a preferred embodiment, the compounds of the formula (I) areadministered to mammals.

In another preferred embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds and particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” means that the compounds of the formula (I) are effectivein reducing the incidence of the particular parasite in an animalinfected with such parasites to an innocuous degree. More specifically,“controlling” in the present context means that the compound of theformula (I) can kill the respective parasite, inhibit its growth, orinhibit its proliferation.

Arthropods Include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; fromthe order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.; from the order of the Diptera and thesuborders Nematocerina and Brachycerina, for example Aedes spp.,Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomusspp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp.,Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp.,Tipula spp.; from the order of the Siphonapterida, for example Pulexspp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllusspp.;from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.; and also nuisance and hygienepests from the order of the Blattarida.

Arthropods Further Include:

from the subclass of the Acari (Acarina) and the order of theMetastigmata, for example from the family of Argasidae like Argas spp.,Ornithodorus spp., Otobius spp., from the family of Ixodidae like Ixodesspp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the originalgenus of multi-host ticks); from the order of Mesostigmata likeDermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp.,Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; fromthe order of the Actinedida (Prostigmata), for example Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.;and from the order of the Acaridida (Astigmata), for example Acarusspp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichusspp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

Parasitic Protozoa Include:

Mastigophora (Flagellata), for example Trypanosomatidae, for exampleTrypanosoma b. brucei, T. b. gambiense, T. b. rhodesiense, T.congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T.simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, forexample Trichomonadidae, for example Giardia lamblia, G. canis;Sarcomastigophora (Rhizopoda) such as Entamoebidae, for exampleEntamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp.,Harmanella sp.;Apicomplexa (Sporozoa) such as Eimeridae, for example Eimeriaacervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E.arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E.chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E.debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E.flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina,E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E.ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E.stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii,Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I.rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec.,in particular C. parvum; such as Toxoplasmadidae, for example Toxoplasmagondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; suchas Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S.ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such asLeucozoidae, for example Leucozytozoon simondi, such as Plasmodiidae,for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P. spec., such as Piroplasmea, for example Babesia argentina, B.bovis, B. canis, B. spec., Theileria parva, Theileria spec., such asAdeleina, for example Hepatozoon canis, H. spec.

Pathogenic endoparasites which are helminths include Platyhelmintha(e.g. Monogenea, cestodes and trematodes), nematodes, Acanthocephala,and Pentastoma. These include:

Monogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystomaspp.;

Cestodes: from the order of the Pseudophyllidea for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diphlogonoporus spp.;

from the order of the Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;Trematodes: from the class of the Digenea, for example: Diplostomumspp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hyporaeum spp., Fasciola spp.,Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelumspp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp.,Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylusspp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp.,Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp.,Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp.,Metorchis spp., Heterophyes spp., Metagonimus spp.;Nematodes: Trichinellida, for example: Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.,from the order of the Tylenchida, for example: Micronema spp.,Strongyloides spp.;from the order of the Rhabditida, for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.,Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.from the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example: Filicollis spp.; from the order of theMoniliformida, for example: Moniliformis spp.;from the order of the Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.;Pentastoma: from the order of the Porocephalida, for example Linguatulaspp.

In the veterinary field and in animal keeping, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic ortherapeutic.

Thus, one embodiment of the present invention refers to the use of acompound of the formula (I) as a medicament.

A further aspect refers to the use of a compound of the formula (I) asan antiendoparasitic agent, in particular a helminthicidal agent orantiprotozoic agent. Compounds of the formula (I) are suitable for useas an antiendoparasitic agent, especially as a helminthicidal agent orantiprotozoic agent, for example in animal breeding, in animalhusbandry, in animal houses and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula(I) as an antiectoparasitic, in particular an arthropodicide such as aninsecticide or an acaricide. A further aspect relates to the use of acompound of the formula (I) as an antiectoparasitic, in particular anarthropodicide such as an insecticide or an acaricide, for example inanimal husbandry, in animal breeding, in animal houses or in the hygienesector.

Anthelmintic Mixing Components

The following anthelmintic mixing components may be mentioned by way ofexample:

anthelmintically active compounds including trematicidally andcestocidally active compounds:

from the class of the macrocyclic lactones, for example: abamectin,doramectin, emamectin, eprinomectin, ivermectin, milbemycin, moxidectin,nemadectin, selamectin;

from the class of the benzimidazoles and probenzimidazoles, for example:albendazole, albendazole-sulphoxide, cambendazole, cyclobendazole,febantel, fenbendazole, flubendazole, mebendazole, netobimin,oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate,triclabendazole;from the class of the cyclooctadepsipeptides, for example: emodepside,PF1022;from the class of the aminoacetonitrile derivatives, for example:monepantel;from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;from the class of the salicylanilides, for example: bromoxanide,brotianide, clioxanide, closantel, niclosamide, oxyclozanide,rafoxanide, tribromsalan;from the class of the paraherquamides, for example: derquantel,paraherquamide;from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;from the class of the organophosphates, for example: coumaphos,crufomate, dichlorvos, haloxone, naphthalofos, trichlorfon;from the class of the substituted phenols, for example: bithionol,disophenol, hexachlorophene, niclofolan, meniclopholan, nitroxynil;from the class of the piperazinones, for example: praziquantel,epsiprantel;from various other classes, for example: amoscanate, bephenium,bunamidine, clonazepam, clorsulon, diamfenetid, dichlorophen,diethylcarbamazine, emetine, hetolin, hycanthone, lucanthone, Miracil,mirasan, niclosamide, niridazole, nitroxynil, nitroscanate, oltipraz,omphalotin, oxamniquin, paromomycin, piperazine, resorantel.Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host or after injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of worms;    -   Aedes: yellow fever, dengue fever, filariasis, other viral        diseases;    -   Simulidae: transmission of worms, in particular Onchocerca        volvulus;        2) Lice: skin infections, epidemic typhus;        3) Fleas: plague, endemic typhus;        4) Flies: sleeping sickness (trypanosomiasis); cholera, other        bacterial diseases;        5) Mites: acariosis, epidemic typhus, rickettsialpox,        tularaemia, Saint Louis encephalitis, tick-borne encephalitis        (TBE), Crimean-Congo haemorrhagic fever, borreliosis;        6) Ticks: borellioses such as Borrelia duttoni, tick-borne        encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia        canis canis).

Examples of vectors in the context of the present invention are insects,such as aphids, flies, leafhoppers or thrips, which can transmit plantviruses to plants. Other vectors capable of transmitting plant virusesare spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, lice, fleas, flies, mites and ticks, whichcan transmit pathogens to animals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, inforestry, in gardens and in leisure facilities, and also in theprotection of materials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. it can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic protection sector, in the hygiene protection sectorand in the protection of stored products, particularly for control ofinsects, arachnids and mites encountered in enclosed spaces, for exampledwellings, factory halls, offices, vehicle cabins. For controllinganimal pests, the compounds of the formula (I) are used alone or incombination with other active compounds and/or auxiliaries. They arepreferably used in domestic insecticide products. The compounds of theformula (I) are effective against sensitive and resistant species, andagainst all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

Preparation ExamplesN-[5-Ethylsulphonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]thioacetamide(Ex. 63)

71 mg (0.16 mmol) ofN-[5-ethylsulphonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]acetamidewere dissolved in 6 ml of toluene, 65.8 mg (0.16 mmol) of Lawesson'sreagent (4-methoxyphenyldithiophosphonic anhydride) were added and themixture was stirred at 90° C. for 3 h. Subsequently, a further 197.5 mg(0.48 mmol) of Lawesson's reagent were added and the mixture was stirredat 90° C. for 1 h. The solvent was distilled off under reduced pressureand the residue was purified by column chromatography using acyclohexane/ethyl acetate gradient (30:70 to 0:100) as mobile phase.

(log P (neutral): 2.41; MH⁺: 444; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.19(t, 3H), 2.74 (s, 3H), 3.68 (q, 2H), 3.91 (s, 3H), 8.31 (s, 1H), 8.59(d, 1H), 9.30 (s, 1H), 9.35 (br. s, 1H), 12.69 (s, 1H).

N-[5-Ethylsulphonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]acetamide

774 mg (1.80 mmol) of5-(ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-aminewere initially charged with 220.8 mg of 4-dimethylaminopyridine (1.80mmol) in a mixture of 20 ml each of pyridine and toluene, and 425.7 mg(5.42 mmol) of acetyl chloride were added. The reaction mixture wasstirred at 100° C. for 45 min, the solvent was distilled off underreduced pressure and the residue was purified by column chromatographyusing cyclohexane/ethyl acetate as mobile phase.

(log P (neutral): 2.01; MH⁺: 428; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.15(t, 3H), 2.17 (s, 3H), 3.62 (q, 2H), 3.88 (s, 3H), 8.29 (s, 1H),8.46-8.53 (m, 2H), 9.29 (s, 1H), 11.31 (s, 1H).

N-{5-(Ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-yl}-2-methylpropanamide(Ex. 16)

54 mg (0.11 mmol) of5-(ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-aminewere dissolved in 4 ml of acetonitrile, 360 mg of pyridine (4.54 mmol)and 13.87 mg of 4-dimethylaminopyridine (0.11 mmol) were added and themixture was heated to 60° C. 123.4 mg (1.13 mmol) of 2-methylpropionylchloride were then added, the heating bath was removed and the mixturewas stirred at room temperature overnight. The reaction was diluted with10 ml of dichloromethane, washed with 1 M hydrochloric acid solution anddried over sodium sulphate, and the solvent was then distilled off underreduced pressure. The residue was purified by column chromatographyusing cyclohexane/ethyl acetate (1:1) as mobile phase.

(log P (neutral): 2.61; MH⁺: 456; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm:1.11-1.19 (m, 9H), 2.75-2.81 (m, 1H), 3.61 (q, 2H), 3.87 (s, 3H), 8.30(s, 1H), 8.47 (d, 1H), 8.55 (d, 1H), 9.29 (s, 1H), 11.27 (s, 1H).

5-(Ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-amine(Ex. 14)

118 mg (0.29 mmol) of2-(6-chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine,3 ml of ethanol and 3 ml of 26% strength aqueous ammonia solution werestirred in a microwave oven at 120° C. and 15 bar for 6 h. The mixturewas freed of the solvent under reduced pressure and the residue was useddirectly for the next step.

(log P (neutral): 1.62; MH⁺: 386; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.13(t, 3H), 3.46 (q, 2H), 3.82 (s, 3H), 6.76 (d, 1H), 7.42 (br. s., 2H),7.93 (d, 1H), 8.24 (s, 1H), 9.23 (s, 1H).

2-(6-Chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(Ex. XIII-1)

900 mg (2.41 mmol) of2-(6-chloro-3-ethylsulphanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridinewere dissolved in 50 ml of dichloromethane, 555.6 mg (12.0 mmol) offormic acid and 1.64 g (16.8 mmol) of 35% strength hydrogen peroxidewere added at room temperature and the mixture was then stirred at roomtemperature for 5 h. The mixture was diluted with water and sodiumbisulfite solution was added, the mixture was stirred for 1 h andsaturated sodium bicarbonate solution was then added. The organic phasewas separated off, the aqueous phase was extracted twice withdichloromethane and the combined organic phases were then freed of thesolvent under reduced pressure. The residue was purified by columnchromatography by means of preparative HPLC using a water/acetonitrilegradient as eluent.

(log P (neutral): 2.54; MH⁺: 405; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.77 (q, 2H), 3.91 (s, 3H), 8.13 (d, 1H), 8.32 (s, 1H), 8.56(d, 1H), 9.30 (s, 1H).

2-(6-Chloro-3-ethylsulphanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(Ex. XI-1)

4.00 g (10.7 mmol) of2-(3,6-dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridinewere dissolved in 60 ml of tetrahydrofuran, 446 mg (11.1 mmol) of sodiumhydride were added at −5° C. and the mixture was stirred at 0° C. for 30minutes. 733 mg (11.8 mmol) of ethanethiol were then added dropwise over30 minutes at −5° C., the cooling bath was removed and the mixture wasstirred at room temperature for 2 h. The reaction mixture was hydrolysedwith water, the organic phase was separated off and the aqueous phasewas extracted twice with ethyl acetate. The organic phases werecombined, washed with sodium chloride solution and dried over sodiumsulphate, and the solvent was then distilled off under reduced pressure.The residue was purified by trituration with methyl tert-butylketone/dichloromethane 25:1.

(log P (neutral): 3.06; MH⁺: 373

2-(3,6-Dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(Ex. IX-1)

20 g (104.6 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine,25.11 g (130.8 mmol) of 3,6-dichloropyridine-2-carboxylic acid and 20.06g (104.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 200 ml of pyridine at 120° C. for 8h. The reaction mixture was freed of solvent under reduced pressure,water was added and the mixture was extracted three times with ethylacetate. The organic phases were combined and dried over sodiumsulphate, and the solvent was then distilled off under reduced pressure.The residue was purified by column chromatography using acyclohexane/ethyl acetate gradient as mobile phase.

(log P (neutral): 2.81; MH⁺: 347; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 3.99(s, 3H), 7.89 (d, 1H), 8.32 (s, 1H), 8.35 (d, 1H), 9.28 (s, 1H).

N-{5-(Ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-yl}methanesulphonamide(Ex. 26)

66 mg (0.13 mmol) of5-(ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-aminewere dissolved in 5 ml of acetonitrile, 439 mg (5.54 mmol) of pyridineand 17.0 mg (0.13 mmol) of 4-dimethylaminopyridine were added, and 124.6mg (0.69 mmol) of methanesulphonic anhydride were added dropwise underargon. The mixture was stirred at room temperature for 2 h, another124.6 mg (0.69 mmol) of methanesulphonic anhydride were added and themixture was stirred at 60° C. for 2 h. The solvent was distilled off andthe residue was dissolved in dichloromethane and washed with 2 Nhydrochloric acid solution. The aqueous phase was extracted twice withdichloromethane, the combined organic phases were dried over sodiumsulphate and the solvent was then distilled off under reduced pressure.The residue was purified by column chromatography using awater/acetonitrile gradient as mobile phase.

(log P (neutral): 0.85; MH⁺: 464; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.34 (s, 3H), 3.74 (q, 2H), 3.92 (s, 3H), 7.34 (d, 1H), 8.29(s, 1H), 8.40 (d, 1H), 9.29 (s, 1H), 11.72 (s, 1H).

1-[5-Ethylsulphonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]-1,2-dimethylhydrazine(Ex. 60)

Under argon, 102 mg (0.25 mmol) of2-(6-chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridinewere dissolved in 7 ml of acetonitrile, 150.9 mg (1.09 mmol) ofpotassium carbonate and 103.8 mg (0.78 mmol) of 1,2-dimethylhydraziniumdichloride were added and the mixture was stirred at room temperaturefor 4 h. The mixture was filtered off and the mother liquor was freed ofthe solvent. The residue was taken up in dichloromethane and washed oncewith water. The organic phase was dried over sodium sulphate, and thesolvent was then distilled off under reduced pressure.

(log P (neutral): 2.39; MH⁺: 429; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.15(t, 3H), 2.54 (d, 3H), 3.23 (s (3H), 3.54 (q, 2H), 3.87 (s, 3H), 5.24(q, 1H), 7.37 (d, 1H), 8.02 (d, 1H), 8.25 (s, 1H), 9.25 (s, 1H).

2-(3,6-Difluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. IX-2)

5.39 g (23.6 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine,4.90 g (30.8 mmol) of 3,6-difluoropyridine-2-carboxylic acid and 4.54 g(23.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 50 ml of pyridine at 120° C. for 8h. The reaction mixture was freed of solvent under reduced pressure,water was added and the mixture was extracted three times with ethylacetate. The organic phases were combined and dried over sodiumsulphate, and the solvent was then distilled off under reduced pressure.The residue was purified by column chromatography using acyclohexane/acetone gradient as mobile phase.

log P (neutral): 2.11; MH⁺: 315; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 4.14(s, 3H), 7.60-7.64 (m, 1H), 8.27-8.33 (m, 2H), 9.28 (s, 1H).

2-[3-(Ethylsulphanyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. XI-2)

6.12 g (19.4 mmol) of2-(3,6-difluoropyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere dissolved in 200 ml of tetrahydrofuran, and 857 mg (21.4 mmol) ofsodium hydride were added at 0° C. 1.67 mg (19.8 mmol) of sodiumthioethoxide were then added, and the mixture was stirred at roomtemperature overnight. Water was added and the reaction mixture wasextracted three times with ethyl acetate. The organic phases werecombined and dried over sodium sulphate, and the solvent was thendistilled off under reduced pressure. The residue was purified by columnchromatography using a cyclohexane/acetone gradient as mobile phase.

log P (neutral): 2.73; MH⁺: 357; 1H-NMR (400 MHz, D6-DMSO) δ ppm: 1.18(t, 3H), 3.01 (q, 2H), 4.00 (s, 3H), 7.49-7.52 (m, 1H), 8.28-8.32 (m,2H), 9.25 (s, 1H).

2-[3-(Ethylsulphonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. XIII-2)

3.68 g (10.2 mmol) of2-[3-(ethylsulphanyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere dissolved in 100 ml of dichloromethane. At room temperature, 3.79 g(75% strength, 16.4 mmol) of meta-chloroperbenzic acid were added andthe mixture was stirred overnight. Saturated sodium thiosulphatesolution and then saturated sodium bicarbonate solution were added tothe mixture. The organic phase was separated off, the aqueous phase wasextracted twice with dichloromethane and the combined organic phaseswere then freed of the solvent under reduced pressure. The residue waspurified by column chromatography by means of preparative HPLC using awater/acetonitrile gradient as eluent.

log P (neutral): 2.30; MH⁺: 389; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.77 (q, 2H), 3.91 (s, 3H), 7.79-7.82 (m, 1H), 8.31 (s, 1H),8.70-8.74 (m, 1H), 9.29 (s, 1H).

2-[6-Ethoxy-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 10)

23 μl (0.38 mmol) of ethanol were initially charged in 5 ml oftetrahydrofuran, and 15 mg (60% strength, 0.38 mmol) of sodium hydridewere added. 100 mg (0.25 mmol) of2-[3-(ethylsulphonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere added and the mixture was stirred at room temperature overnight.Water was added to the mixture. The organic phase was separated off, theaqueous phase was extracted twice with ethyl acetate and the combinedorganic phases were then freed of the solvent under reduced pressure.The residue was purified by column chromatography by means ofpreparative HPLC using a water/acetonitrile gradient as eluent.

log P (neutral): 2.86; MH⁺: 415; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.18(t, 3H), 1.35 (t, 3H), 3.69 (q, 2H), 3.91 (s, 3H), 4.42 (q, 2H), 7.30(d, 1H), 8.28 (s, 1H), 8.34 (d, 1H), 9.29 (s, 1H).

2-[6-(Ethylsulphanyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 5)

32 mg (0.38 mmol) of sodium thioethoxide were initially charged in 5 mlof tetrahydrofuran, and 15 mg (60% strength, 0.38 mmol) of sodiumhydride were added. 100 mg (0.25 mmol) of2-[3-(ethylsulphonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere added and the mixture was stirred at room temperature overnight.Methanol was added and the mixture was then concentrated to dryness. Theresidue was taken up in water and ethyl acetate. The organic phase wasseparated off, the aqueous phase was extracted twice with ethyl acetateand the combined organic phases were then freed of the solvent underreduced pressure. The residue was purified by column chromatography bymeans of preparative HPLC using a water/acetonitrile gradient as eluent.

log P (neutral): 3.14; MH⁺: 431; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.19(t, 3H), 1.30 (t, 3H), 3.20 (q, 2H), 3.71 (q, 2H), 3.90 (s, 3H), 7.82(d, 1H), 8.25 (d, 1H), 8.29 (s, 1H), 9.29 (s, 1H).

2-[3,6-Bis(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 15)

171 mg (0.39 mmol) of2-[6-(ethylsulphanyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere dissolved in 7 ml of dichloromethane, 101 mg (0.43 mmol) ofmeta-chloroperbenzoic acid were then added and the mixture was stirredat room temperature for 1 h. The mixture was washed once with saturatedsodium thiosulphate solution and then with saturated sodium bicarbonatesolution. The organic phase was dried over sodium sulphate, and thesolvent was then distilled off under reduced pressure. The residue waspurified by column chromatography using a water/acetonitrile gradient asmobile phase.

log P (neutral): 2.27; MH⁺: 463; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm:1.18-1.26 (m, 6H), 3.59 (q, 2H), 3.90 (q, 2H), 3.95 (s, 3H), 8.33 (d,1H), 8.56 (d, 1H), 8.89 (d, 1H), 9.31 (s, 1H).

2-[6-(Ethylsulphinyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 37)

171 mg (0.39 mmol) of2-[6-(ethylsulphanyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere dissolved in 7 ml of dichloromethane, 101 mg (0.43 mmol) ofmeta-chloroperbenzoic acid were then added and the mixture was stirredat room temperature for 1 h. The mixture was washed once with saturatedsodium thiosulphate solution and then with saturated sodium bicarbonatesolution. The organic phase was dried over sodium sulphate, and thesolvent was then distilled off under reduced pressure. The residue waspurified by column chromatography using a water/acetonitrile gradient asmobile phase.

log P (neutral): 2.02; MH⁺: 447; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.12(t, 3H), 1.22 (t, 3H), 2.98-3.05 (m, 2H), 3.78-3.87 (m, 2H), 3.90 (s,3H), 8.32 (s, 1H), 8.38 (d, 1H), 8.82 (d, 1H), 9.30 (s, 1H).

2-[6-(S-Ethylsulphonimidoyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 41)

76 mg (0.17 mmol) of2-[6-(ethylsulphinyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere dissolved in 2 ml of acetonitrile, 41 mg (0.20 mmol) of4-nitrobenzenesulphonamide and 88 mg (0.27 mmol) of diacetoxyiodobenzenewere then added and the mixture was stirred at 77° C. for 72 h. Another88 mg (0.27 mmol) of diacetoxyiodobenzene were then added, and themixture was stirred at 77° C. for a further 72 h. This gave the productwhich was purified by distillative removal of the solvent under reducedpressure and by column chromatography of the residue using awater/acetonitrile gradient as mobile phase.

log P (neutral): 1.79; MH⁺: 462; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.19(t, 3H), 1.25 (t, 3H), 3.39-3.51 (m, 2H), 3.90 (q, 2H), 3.94 (s, 3H),8.34 (s, 1H), 8.54 (d, 1H), 8.85 (d, 1H), 9.32 (s, 1H).

2-[3-(Ethylsulphonyl)-6-(methylsulphanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 28)

27 mg (0.38 mmol) of sodium thiomethoxide were initially charged in 5 mlof tetrahydrofuran, and 15 mg (60% strength, 0.38 mmol) of sodiumhydride were added. 100 mg (0.25 mmol) of2-[3-(ethylsulphonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere added and the mixture was stirred at room temperature overnight.Methanol was added and the mixture was then concentrated to dryness. Theresidue was taken up in water and ethyl acetate. The organic phase wasseparated off, the aqueous phase was extracted twice with ethyl acetateand the combined organic phases were then freed of the solvent underreduced pressure. The residue was purified by column chromatographyusing a water/acetonitrile gradient as mobile phase.

log P (neutral): 2.75; MH⁺: 417; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.19(t, 3H), 2.60 (s, 3H), 3.72 (q, 2H), 3.90 (s, 3H), 7.85 (d, 1H), 8.27(d, 1H), 8.29 (s, 1H), 9.29 (s, 1H).

[{5-(Ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridin-2-yl}(methyl)-lambda4-sulphanylidene]cyanamide(Ex. 43)

410 mg (0.98 mmol) of2-[3-(ethylsulphonyl)-6-(methylsulphanyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere initially charged in 40 ml of methanol, and 54 mg (1.28 mmol) ofcyanamide and 133 mg (1.18 mmol) of potassium tert-butoxide were added.263 mg (1.47 mmol) of N-bromosuccinimide were then added a little at atime, and the mixture was stirred at room temperature overnight. Themixture was concentrated, and saturated sodium thiosulphate solution anddichloromethane were then added. The organic phase was separated off,the aqueous phase was extracted twice with dichloromethane and thecombined organic phases were then freed of the solvent under reducedpressure. The residue was purified by column chromatography using awater/acetonitrile gradient as mobile phase.

log P (neutral): 1.75; MH⁺: 457; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.24(t, 3H), 3.29 (s, 3H), 3.87-3.94 (m, 2H), 3.98 (s, 3H), 8.34 (s, 1H),8.57 (d, 1H), 8.89 (d, 1H), 9.33 (s, 1H).

2-[6-(Benzylsulphanyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 30)

64 mg (0.51 mmol) of benzylmercaptan were initially charged in 10 ml oftetrahydrofuran, and 31 mg (60% strength, 0.77 mmol) of sodium hydridewere added. 200 mg (0.51 mmol) of2-[3-(ethylsulphonyl)-6-fluoropyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere added and the mixture was stirred at room temperature overnight.Methanol was added and the mixture was then concentrated to dryness. Theresidue was taken up in water and ethyl acetate. The organic phase wasseparated off, the aqueous phase was extracted twice with ethyl acetateand the combined organic phases were then freed of the solvent underreduced pressure. The residue was purified by column chromatographyusing a water/acetonitrile gradient as mobile phase.

log P (neutral): 3.72; MH⁺: 493; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.18(t, 3H), 3.69 (q, 2H), 3.80 (s, 3H), 4.49 (s, 2H), 7.23-7.39 (m, 5H),7.87 (d, 1H), 8.27 (d, 1H), 8.30 (s, 1H), 9.29 (s, 1H).

5-(Ethylsulphonyl)-N-isopropyl-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-sulphonamide(Ex. 49)

520 mg (1.05 mmol) of2-[6-(benzylsulphanyl)-3-(ethylsulphonyl)pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere initially charged in a mixture of 10 ml of dichloromethane, 2 ml ofwater and 1 ml of acetic acid at 0° C., and 624 mg (3.16 mmol) of1,3-dichloro-5,5-dimethylhydantoin, dissolved in dichloromethane, wereadded dropwise. The mixture was stirred at room temperature overnight.The organic phase was separated off and the aqueous phase was extractedtwice with dichloromethane. At 0° C., a quarter of the combined organicdichloromethane solution was added dropwise to a solution ofisopropylamine (0.028 ml, 0.33 mmol) in 2 ml of tetrahydrofuran. Themixture was stirred at room temperature for 3 h and then concentrated todryness on a rotary evaporator. The residue was purified by columnchromatography using a water/acetonitrile gradient as mobile phase.

log P (neutral): 2.49; MH⁺: 492; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.01(d, 6H), 1.22 (t, 3H), 3.45-3.53 (m, 1H), 3.84 (q, 2H), 3.93 (s, 3H),8.29 (bs, 1H), 8.35 (s, 1H), 8.45 (d, 1H), 8.82 (d, 1H), 9.35 (s, 1H).

2-{6-[(E)-2-Cyclopropylvinyl]-3-(ethylsulphonyl)pyridin-2-yl}-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(Ex. 40)

100 mg (0.25 mmol) of2-(6-chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine,48 mg (0.25 mmol) of (E)-2-cyclopropylvinylboronic acid pinacol esterand 9 mg (0.007 mmol) of tetrakis(triphenylphosphine)palladium(0) wereinitially charged in a mixture of degassed dioxane (2 ml) and degassedsodium carbonate solution (1M, 1 ml), and the mixture was stirred at 96°C. for 16 h. The reaction mixture was then cooled to room temperatureand concentrated under reduced pressure, and the residue was taken up inwater and dichloromethane. The phases were separated and the aqueousphase was extracted three times with dichloromethane. The combinedorganic phases were then freed of the solvent and the residue waspurified by column chromatography using a water/acetonitrile gradient asmobile phase.

log P (neutral): 3.24; MH⁺: 437; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm:0.67-0.69 (m, 2H), 0.91-0.96 (m, 2H), 1.18 (t, 3H), 1.72-1.76 (m, 1H),3.69 (q, 2H), 3.86 (s, 3H), 6.60 (dd, 1H), 6.81 (d, 1H), 7.82 (d, 1H),8.28 (s, 1H), 8.39 (d, 1H), 9.28 (s, 1H).

Methyl5-(ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylate(Ex. 12)

In an autoclave, 1.98 g (4.88 mmol) of2-(6-chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine,749 mg (9.12 mmol) of sodium acetate and 386 mg (0.48 mmol) of[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-acetonecomplex were initially charged in 100 ml of methanol, and the mixturewas carbonylated at 80° C. under a carbon monoxide atmosphere at apressure of 10 bar for 15 h. The mixture was then cooled to roomtemperature and the carbon monoxide atmosphere was removed. The reactionmixture was concentrated under reduced pressure and the residue wastaken up in water and dichloromethane. The phases were separated and theaqueous phase was extracted three times with dichloromethane. Thecombined organic phases were then freed of the solvent and the residuewas purified by column chromatography using a water/acetonitrilegradient as mobile phase.

log P (neutral): 2.17; MH⁺: 429; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.81 (q, 2H), 3.89 (s, 3H), 3.96 (s, 3H), 8.32 (s, 1H), 8.54(d, 1H), 8.75 (d, 1H), 9.30 (s, 1H).

5-(Ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylicacid

944 mg (2.20 mmol) of methyl5-(ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylatewere initially charged in 10 ml of ethanol, 2.42 ml of aqueous sodiumhydroxide solution (1M, 2.42 mmol) were added and the mixture wasstirred at room temperature for 30 min. The reaction mixture wasconcentrated under reduced pressure and the residue was taken up inwater. The mixture was then acidified with dilute hydrochloric acid andthe precipitated solid was filtered off with suction, washed with waterand dried.

log P (neutral): 0.76; MH⁺: 415; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.81 (q, 2H), 3.90 (s, 3H), 8.32 (s, 1H), 8.49 (d, 1H), 8.71(d, 1H), 9.30 (s, 1H).

5-(Ethylsulphonyl)-N-methyl-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxamide(Ex. 31)

200 mg (0.48 mmol) of5-(ethylsulphonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxylicacid were initially charged in 10 ml of dioxane, 111 mg of1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 0.57mmol) were added and the mixture was stirred at room temperature for 1h. 0.24 ml of methanamine solution (2M in THF, 0.48 mmol) were thenadded and the reaction mixture was stirred at room temperature for 16 h.The mixture was concentrated under reduced pressure and the residue wastaken up in water and dichloromethane. The phases were separated and theaqueous phase was extracted three times with dichloromethane. Thecombined organic phases were then freed of the solvent and the residuewas purified by column chromatography using a water/acetonitrilegradient as mobile phase.

log P (neutral): 1.96; MH⁺: 428; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.19(t, 3H), 2.84 (d, 3H), 3.82 (q, 2H), 3.93 (s, 3H), 8.33 (s, 1H), 8.49(d, 1H), 8.72 (d, 1H), 8.95-8.98 (m, 1H), 9.36 (s, 1H).

5-(Ethylsulphonyl)-N-methyl-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carbothioamide(Ex. 34)

20 mg (0.05 mmol) of5-(ethylsulphonyl)-N-methyl-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]pyridine-2-carboxamidewere initially charged in 2 ml of toluene, 8 mg (0.02 mmol) ofLawesson's reagent (4-methoxyphenyldithiophosphonic anhydride) wereadded and the mixture was stirred under reflux for 10 h. A further 8 mg(0.02 mmol) of Lawesson's reagent were then added and the reactionmixture was stirred at 106° C. for 16 h. A further 16 mg (0.04 mmol) ofLawesson's reagent were subsequently added and the reaction mixture wasstirred at 106° C. for a further 16 h. The mixture was cooled to roomtemperature and concentrated under reduced pressure. The residue waspurified by column chromatography using a water/acetonitrile gradient asmobile phase.

log P (neutral): 2.76; MH⁺: 444; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.22 (d, 3H), 3.80 (q, 2H), 3.92 (s, 3H), 8.33 (s, 1H), 8.70(d, 1H), 8.88 (d, 1H), 9.36 (s, 1H).

In analogy to the examples and according to the above-describedpreparation processes, the following compounds of the formula (I) can beobtained:

where the substituents R¹, R^(2a), R^(2b), R³, A¹, A², A⁴ and n have themeanings given in the table below:

Ex. R¹ n A⁴ A² A¹ R^(2a) R³ R^(2b) 1 ethyl 0 CH N-methyl N H CF₃

2 ethyl 1 CH N-methyl N H CF₃

3 ethyl 2 CH N-methyl N H CF₃

4 ethyl 2 CH N-methyl N H CF₃

5 ethyl 2 CH N-methyl N H CF₃

6 ethyl 0 CH N-methyl N H CF₃

7 ethyl 2 CH N-methyl N H CF₃

8 ethyl 2 CH N-methyl N H CF₃

9 ethyl 1 CH N-methyl N H CF₃

10 ethyl 2 CH N-methyl N H CF₃

12 ethyl 2 CH N-methyl N H CF₃

13 ethyl 2 CH N-methyl N H CF₃

14 ethyl 2 CH N-methyl N H CF₃

15 ethyl 2 CH N-methyl N H CF₃

16 ethyl 2 CH N-methyl N H CF₃

17 ethyl 2 CH N-methyl N H CF₃

18 ethyl 2 CH N-methyl N H CF₃

19 ethyl 0 CH N-methyl N H CF₃

20 ethyl 2 CH N-methyl N H CF₃

21 ethyl 2 CH N-methyl N H CF₃

22 ethyl 2 CH N-methyl N H CF₃

24 ethyl 2 CH N-methyl N H CF₃

25 ethyl 2 CH N-methyl N H CF₃

26 ethyl 2 CH N-methyl N H CF₃

27 ethyl 0 CH N-methyl N H CF₃

28 ethyl 2 CH N-methyl N H CF₃

29 ethyl 2 CH N-methyl N H CF₃

30 ethyl 2 CH N-methyl N H CF₃

31 ethyl 2 CH N-methyl N H CF₃

32 ethyl 2 CH N-methyl N H CF₃

33 ethyl 2 CH N-methyl N H CF₃

34 ethyl 2 CH N-methyl N H CF₃

35 ethyl 2 CH N-methyl N H CF₃

36 ethyl 2 CH N-methyl N H CF₃

37 ethyl 2 CH N-methyl N H CF₃

38 ethyl 2 CH N-methyl N H CF₃

39 ethyl 2 CH N-methyl N H CF₃

40 ethyl 2 CH N-methyl N H CF₃

41 ethyl 2 CH N-methyl N H CF₃

42 ethyl 2 CH N-methyl N H CF₃

43 ethyl 2 CH N-methyl N H CF₃

44 ethyl 2 CH N-methyl N H CF₃

45 ethyl 2 CH N-methyl N H CF₃

46 ethyl 2 CH N-methyl N H CF₃

47 ethyl 2 CH N-methyl N H CF₃

48 ethyl 2 CH N-methyl N H CF₃

49 ethyl 2 CH N-methyl N H CF₃

50 ethyl 2 CH N-methyl N H CF₃

51 ethyl 2 CH N-methyl N H CF₃

52 ethyl 2 CH N-methyl N H CF₃

53 ethyl 2 CH N-methyl N H CF₃

54 ethyl 2 CH N-methyl N H CF₃

55 ethyl 2 CH N-methyl N H CF₃

56 ethyl 2 CH N-methyl N H CF₃

57 ethyl 2 CH N-methyl N H CF₃

58 ethyl 2 CH N-methyl N H CF₃

59 ethyl 2 CH N-methyl N H CF₃

60 ethyl 2 CH N-methyl N H CF₃

61 ethyl 2 CH N-methyl N H CF₃

62 ethyl 2 CH N-methyl N H C₂F₅

63 ethyl 2 CH N-methyl N H CF₃

64 ethyl 2 CH N-methyl N H CF₃

65 ethyl 2 CH N-methyl N H CF₃

66 ethyl 2 CH N-methyl N H CF₃

67 ethyl 2 CH N-methyl N H C₂F₅

68 ethyl 2 CH N-methyl N H CF₃

69 ethyl 2 CH N-methyl N H CF₃

70 ethyl 2 CH N-methyl N H CF₃

71 ethyl 2 CH N-methyl N H CF₃

72 ethyl 2 CH N-methyl N H CF₃

73 ethyl 2 CH N-methyl N H CF₃

74 ethyl 2 CH N-methyl N H CF₃

where the bond to the remainder of the molecule is identified by a wavyline.

The log P values are measured according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C18). Temperature: 55° C.

The LC-MS determination in the acidic range is effected at pH 2.7 using0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) aseluents, linear gradient from 10% acetonitrile to 95% acetonitrile.Called log P (HCOOH) in the table.

LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.Called log P (neutral) in the table.

Calibration is carried out using unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR data of selected examples are listed either in conventional form(6 values, multiplet splitting, number of hydrogen atoms) or as NMR peaklists.

In each case, the solvent in which the NMR spectrum is recorded isstated.

NMR Peak List Method

The ¹H NMR data of selected examples are stated in the form of ¹H NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The pairs of δvalue-signal intensity numbers for different signal peaks are listedwith separation from one another by semicolons.

The peak list for one example therefore has the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

Calibration of the chemical shift of ¹H NMR spectra is accomplishedusing tetramethylsilane and/or the chemical shift of the solvent,particularly in the case of spectra which are measured in DMSO.Therefore, the tetramethylsilane peak may but need not occur in NMR peaklists.

The lists of the ¹H NMR peaks are similar to the conventional ¹H-NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds which likewiseform part of the subject-matter of the invention, and/or peaks ofimpurities.

In the reporting of compound signals within the delta range of solventsand/or water, our lists of ¹H NMR peaks show the standard solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the peak picking in question in conventional ¹H NMRinterpretation.

Further details of ¹H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

logP- logP- neutral acidic 2.79 2.80 Example 1: ¹H-NMR(400.0 MHz,d₆-DMSO): = 11.055(2.7); 9.258(4.0); 8.289(2.9); 8.278(4.5); 8.267(3.5);8.105(3.0); 8.083(2.4); 5.754(1.4); 3.982 (16.0); 3.318(23.2);2.964(1.2); 2.946(3.9); 2.928(4.0); 2.909(1.3); 2.671(0.5); 2.524(1.2);2.507 (53.8); 2.502(70.0); 2.498(52.2); 2.334(0.4); 2.329(0.5);2.325(0.4); 2.004(0.6); 1.999(0.7); 1.988 (1.7); 1.974(0.7); 1.968(0.7);1.398(0.5); 1.175(0.9); 1.170(4.4); 1.151(9.1); 1.133(4.2); 0.864 (3.8);0.854(5.4); 0.836(2.7); 0.146(0.4); 0.008(3.3); 0.000(79.0); −0.149(0.4)2.25 2.33 Example 2: ¹H-NMR(400.0 MHz, d₆-DMSO): = 10.857(3.1);9.323(4.4); 8.506(1.3); 8.484(5.1); 8.470(4.7); 8.448(1.2); 8.314(0.8);8.304(4.8); 5.754 (0.9); 4.370(16.0); 3.480(1.0); 3.461(1.1);3.447(1.2); 3.428(1.1); 3.410(0.3); 3.318(56.2); 3.027 (1.1);3.009(1.3); 2.994(1.1); 2.976(1.0); 2.670(0.7); 2.540(1.8); 2.521(8.7);2.502(111.6); 2.440 (0.4); 2.329(0.7); 1.288(4.0); 1.269(8.3);1.251(3.8); 1.148(4.2); 1.130(8.6); 1.111(4.0); 0.146 (0.4);0.000(73.5); −0.150(0.4) 1.73 2.74 Example 3: ¹H-NMR(400.0 MHz,d₆-DMSO): = 12.789(2.8); 9.309(5.1); 9.278(0.4); 8.647(2.5); 8.625(3.2);8.469(3.3); 8.447(2.6); 8.337(0.4); 8.317 (6.2); 4.020(0.5); 3.988(1.4);3.914(16.0); 3.838(0.9); 3.823(0.9); 3.735(1.3); 3.716(3.8); 3.698(3.9); 3.680(1.3); 3.319(67.3); 2.671(0.7); 2.501(105.6); 2.328(0.7);1.988(0.5); 1.398(0.5); 1.236 (0.4); 1.208(4.1); 1.190(8.3); 1.171(3.9);0.000(0.8) 1.94 3.17 Example 4: ¹H-NMR(400.0 MHz, d₆-DMSO): =12.826(1.4); 9.304(5.0); 8.636(1.2); 8.614(1.7); 8.455(1.8); 8.432(1.5);8.313(5.8); 5.753(0.3); 4.017 (1.1); 3.911(16.0); 3.729(1.1);3.710(3.1); 3.692(3.2); 3.673(1.1); 3.321(93.6); 3.318(98.7); 2.671(1.0); 2.506(132.9); 2.501(174.0); 2.497(132.9); 2.328(1.1); 1.206(4.2);1.188(9.1); 1.169(4.2); 0.008(2.5); 0.000(59.6); −0.008(3.0) 3.14 3.19Example 5: ¹H-NMR(400.0 MHz, d₆-DMSO): = 9.289(4.5); 8.294(4.8);8.264(3.0); 8.242(3.3); 7.832(3.3); 7.811(3.0); 5.754(3.6); 3.898(16.0);3.736 (1.1); 3.718(3.7); 3.700(3.6); 3.681(1.1); 3.321(59.9);3.230(1.2); 3.211(3.9); 3.193(4.0); 3.175 (1.3); 2.672(0.4);2.502(66.8); 2.329(0.4); 1.322(4.3); 1.303(9.0); 1.285(4.2); 1.206(3.8);1.187 (8.2); 1.169(3.7); 0.000(19.2) 3.18 Example 6: ¹H-NMR(400.0 MHz,d₆-DMSO): = 12.184(1.1); 9.269(4.4); 8.314(0.5); 8.291(4.8); 8.220(2.0);8.198(3.3); 8.131(3.5); 8.109(2.2); 4.473 (0.4); 4.037(16.0);3.825(0.3); 3.318(99.5); 3.038(1.2); 3.019(3.9); 3.001(3.9); 2.983(1.3);2.670 (1.5); 2.506(175.4); 2.502(227.7); 2.498(180.7); 2.328(1.5);1.215(4.3); 1.196(8.8); 1.178(4.1); 0.146(0.6); 0.008(8.0);0.000(124.6); −0.150(0.6) 2.66 2.71 Example 7: ¹H-NMR(400.0 MHz,d₆-DMSO): = 11.227(2.9); 9.288(4.2); 8.568(2.5); 8.546(4.5); 8.492(3.9);8.469(2.3); 8.313(0.5); 8.297(4.6); 3.977 (0.3); 3.871(16.0);3.644(1.0); 3.626(3.4); 3.607(3.4); 3.589(1.0); 3.315(48.8); 2.675(0.6);2.670 (0.8); 2.666(0.6); 2.510(49.3); 2.506(95.9); 2.501(126.1);2.497(94.3); 2.493(48.1); 2.364(4.6); 2.347(4.7); 2.332(0.7);2.328(0.9); 2.324(0.7); 1.184(3.6); 1.166(8.0); 1.147(3.5); 1.086(0.6);1.080(0.5); 1.076(0.5); 1.068(0.9); 1.056(0.6); 1.049(0.6); 1.037(0.3);0.507(0.8); 0.497(2.4); 0.493 (2.6); 0.488(1.3); 0.482(1.2); 0.476(2.4);0.472(2.4); 0.462(0.9); 0.211(0.9); 0.198(3.0); 0.186 (3.0); 0.174(0.7);0.008(1.3); 0.000(29.8); −0.008(1.3) 2.12 2.80 Example 8: ¹H-NMR(400.0MHz, d₆-DMSO): = 12.509(2.2); 9.306(4.4); 9.276(0.5); 8.631(2.0);8.609(2.6); 8.470(3.1); 8.448(2.5); 8.358(0.4); 8.336 (0.5); 8.313(5.3);7.899(0.4); 7.877(0.4); 7.026(0.5); 6.910(0.5); 6.898(1.0); 6.884(0.5);6.769 (0.5); 3.988(2.1); 3.913(16.0); 3.725(1.0); 3.707(3.3);3.688(3.4); 3.670(1.0); 3.319(77.3); 3.317 (79.9); 2.675(0.6);2.670(0.8); 2.666(0.6); 2.506(98.6); 2.501(130.7); 2.497(99.3);2.328(0.8); 2.324 (0.6); 1.205(3.7); 1.187(8.2); 1.168(3.6); 0.008(2.4);0.000(59.0); −0.008(2.6) 1.97 2.02 Example 9: ¹H-NMR(400.0 MHz,d₆-DMSO): = 10.912(4.0); 9.324(5.3); 9.155(0.4); 8.535(0.4); 8.523(0.5);8.469(11.0); 8.302(5.5); 8.111(0.6); 7.145(0.9); 6.895(0.5);4.371(16.0); 4.279(0.9); 3.483(1.3); 3.468(1.6); 3.451(1.8); 3.433(1.5);3.418 (0.9); 3.392(0.6); 3.370(2.1); 3.320(285.8); 3.317(258.5);3.315(241.7); 3.247(1.1); 3.227(0.7); 3.045(0.6); 3.028(1.3);3.010(1.5); 2.993(1.4); 2.976(1.1); 2.958(0.5); 2.720(0.4); 2.671(2.6);2.635(0.7); 2.504(353.4); 2.500(340.8); 2.330(2.5); 2.257(0.6);2.211(15.5); 1.372(7.6); 1.328(0.4); 1.290(4.6); 1.272(8.4); 1.254(4.3);1.224(0.4); 0.000(6.6); −0.002(6.1) 2.86 2.94 Example 10: ¹H-NMR(400.0MHz, d₆-DMSO): = 9.285(4.3); 8.349(3.4); 8.326(3.6); 8.282(4.5);7.312(3.6); 7.290(3.5); 5.754(7.8); 4.451(1.3); 4.434 (4.2); 4.416(4.3);4.399(1.3); 3.909(16.0); 3.719(1.1); 3.701(3.6); 3.682(3.6); 3.664(1.1);3.319 (1.9); 2.508(20.7); 2.503(27.3); 2.499(20.9); 1.370(4.3);1.353(8.9); 1.335(4.2); 1.202(3.8); 1.184 (8.1); 1.165(3.7); 0.008(1.8);0.000(32.6); −0.008(1.7) 2.17 2.17 Example 12: ¹H-NMR(400.0 MHz,d₆-DMSO): = 9.301(3.8); 9.282(0.4); 8.762(2.2); 8.741(2.7); 8.549(2.8);8.528(2.3); 8.320(4.1); 8.263(0.4); 4.106 (1.4); 3.959(14.0);3.893(12.6); 3.837(1.0); 3.819(3.0); 3.801(3.0); 3.782(1.0); 3.721(1.4);3.324 (16.6); 2.504(32.9); 2.087(16.0); 1.220(3.2); 1.202(6.6);1.183(3.1); 0.000(9.4) 2.28 2.33 Example 13: ¹H-NMR(400.0 MHz, d₆-DMSO):= 11.265(3.2); 9.290(4.4); 9.279(0.4); 8.548(2.2); 8.525(4.5);8.483(4.4); 8.470(0.4); 8.461(2.1); 8.312 (0.6); 8.297(5.0); 4.454(0.8);4.370(1.1); 3.978(1.3); 3.872(16.0); 3.648(1.0); 3.629(3.5); 3.611(3.6); 3.593(1.1); 3.314(110.7); 2.675(1.1); 2.670(1.4); 2.505(154.7);2.501(204.1); 2.497(159.5); 2.481(7.8); 2.462(4.7); 2.443(1.6);2.420(0.4); 2.328(1.3); 2.324(1.0); 1.269(0.5); 1.184(3.7); 1.165(8.1);1.147(3.9); 1.129(0.7); 1.124(0.6); 1.107(4.4); 1.088(8.8); 1.069(4.0);0.000(51.4) 1.62 1.63 Example 14: ¹H-NMR(400.0 MHz, d₆-DMSO): =9.231(4.1); 8.312(0.7); 8.241(4.3); 7.945(3.0); 7.922(3.2); 7.418(2.7);6.769(3.3); 6.746(3.3); 3.824 (16.0); 3.493(1.0); 3.475(3.3);3.456(3.4); 3.438(1.0); 3.315(179.7); 2.675(1.0); 2.670(1.3); 2.666(1.0); 2.523(3.2); 2.510(71.6); 2.506(145.1); 2.501(198.3);2.497(152.7); 2.492(78.5); 2.332 (0.9); 2.328(1.3); 2.324(0.9);1.150(3.4); 1.132(7.7); 1.114(3.4); 0.000(1.2) 2.28 2.31 Example 15:¹H-NMR(400.0 MHz, d₆-DMSO): = 9.325(4.3); 8.901(3.1); 8.880(3.5);8.574(3.6); 8.554(3.2); 8.345(4.6); 8.314(0.9); 5.754(0.4); 4.036 (0.8);3.951(16.0); 3.933(1.2); 3.914(3.8); 3.908(1.7); 3.896(3.8); 3.877(1.1);3.807(0.4); 3.770 (0.4); 3.622(1.3); 3.604(4.0); 3.585(4.1); 3.567(1.4);3.318(156.6); 2.670(1.6); 2.666(1.3); 2.541 (0.9); 2.506(190.7);2.501(253.5); 2.497(195.6); 2.332(1.2); 2.328(1.6); 2.324(1.3);2.300(0.4); 1.261(4.0); 1.250(5.1); 1.242(9.2); 1.232(10.3); 1.224(4.7);1.213(4.7); 1.198(1.0); 1.179(0.4); 1.066 (0.6); 0.008(1.0); 0.000(31.4)2.61 2.63 Example 16: ¹H-NMR(400.0 MHz, d₆-DMSO): = 11.270(3.0);9.290(4.4); 8.562(2.4); 8.539(4.3); 8.482(3.9); 8.460(2.2); 8.313(0.6);8.298(4.8); 3.873 (16.0); 3.638(1.0); 3.620(3.5); 3.601(3.5);3.583(1.1); 3.316(60.6); 2.822(0.4); 2.805(1.1); 2.788 (1.5);2.770(1.2); 2.754(0.5); 2.675(0.8); 2.671(1.0); 2.506(115.0);2.501(150.5); 2.497(116.9); 2.333(0.7); 2.328(1.0); 1.988(1.0);1.398(0.4); 1.193(0.5); 1.182(3.7); 1.163(8.1); 1.145(3.8); 1.127(15.7);1.110(15.5); 1.066(0.7); 1.049(0.7); 0.146(1.0); 0.008(11.2);0.000(191.8); −0.150 (1.0) 2.69 2.77 Example 17: ¹H-NMR(400.0 MHz,d₆-DMSO): = 14.175(0.7); 14.137(0.6); 9.267(4.1); 8.614(0.5);8.582(0.6); 8.564(0.5); 8.314(0.4); 8.276(4.9); 7.764(0.4); 7.747(0.4);7.664(0.5); 7.647(0.4); 6.902(0.6); 6.680(0.5); 3.823(16.0); 3.800(2.1);3.317 (74.3); 3.279(0.7); 2.671(1.3); 2.502(208.4); 2.328(1.4);1.240(3.5); 1.222(7.3); 1.203(3.4); 0.000 (8.1) 3.22 3.31 Example 18:¹H-NMR(400.0 MHz, d₆-DMSO): = 9.281(4.1); 8.326(3.3); 8.304(3.5);8.281(4.3); 7.256(3.7); 7.233(3.6); 5.754(8.8); 5.344(0.4); 5.329 (1.2);5.314(1.6); 5.298(1.2); 5.283(0.5); 3.907(15.7); 3.703(1.0); 3.685(3.4);3.666(3.5); 3.648 (1.0); 3.318(7.3); 2.511(13.3); 2.507(25.8);2.503(34.4); 2.498(26.3); 2.494(13.6); 1.340(16.0); 1.325(15.9);1.200(3.5); 1.182(7.8); 1.163(3.5); 0.008(2.1); 0.000(40.7); −0.008(2.0)3.36 Example 19: ¹H-NMR(400.0 MHz, d₆-DMSO): = 11.039(3.2); 9.269(4.1);8.396(2.8); 8.374(3.5); 8.287(4.4); 8.186(3.0); 8.164(2.5); 8.076(0.3);8.037 (3.4); 8.019(3.8); 8.015(3.0); 7.634(0.8); 7.616(2.0); 7.597(1.6);7.575(0.3); 7.570(0.4); 7.548 (2.8); 7.528(3.8); 7.510(1.6); 4.495(0.6);4.248(0.4); 4.039(16.0); 4.021(0.4); 3.359(0.4); 3.318 (28.9);3.273(0.5); 3.018(1.3); 2.999(3.9); 2.981(4.0); 2.963(1.3); 2.672(0.3);2.535(0.8); 2.507(37.9); 2.502(48.8); 2.498(37.1); 1.989(0.9);1.398(0.6); 1.312(0.4); 1.208(4.3); 1.190(8.9); 1.171 (4.2); 0.000(5.4)2.98 Example 20: ¹H-NMR(400.0 MHz, d₆-DMSO): = 11.585(1.2); 11.233(3.8);9.334(4.7); 9.311(1.5); 9.255(0.4); 8.685(0.8); 8.663(1.2); 8.580(1.0);8.566(1.5); 8.558(5.8); 8.550(5.5); 8.528(1.0); 8.520(0.5); 8.513(0.4);8.316(5.8); 8.247(0.4); 8.110 (0.5); 8.090(0.5); 8.074(0.5); 8.061(1.5);8.042(1.5); 8.029(3.9); 8.010(4.0); 7.685(0.7); 7.666 (2.2); 7.648(1.9);7.621(0.7); 7.604(3.1); 7.585(4.4); 7.566(1.9); 7.558(1.3); 7.539(1.5);7.520(0.6); 5.753(0.6); 4.494(1.2); 4.418(16.0); 3.928(4.9); 3.716(0.3);3.698(1.1); 3.679(1.1); 3.661(0.4); 3.569(3.3); 3.523(1.0); 3.504(1.3);3.490(1.2); 3.471(1.2); 3.453(0.4); 3.317(61.8); 3.082(0.3); 3.063(1.1); 3.045(1.3); 3.030(1.1); 3.012(1.0); 2.945(0.4); 2.786(0.3);2.672(0.8); 2.502(123.5); 2.329 (0.8); 1.958(0.4); 1.318(3.9);1.299(8.3); 1.281(3.9); 1.254(0.8); 1.235(1.7); 1.220(1.5); 1.201 (2.7);1.183(1.4); 0.000(0.6) 2.17 2.22 Example 21: ¹H-NMR(400.0 MHz, d₆-DMSO):= 11.051(3.0); 9.292(4.2); 8.515(12.5); 8.313(0.6); 8.300(4.6);5.753(2.1); 4.147(11.0); 4.108(0.6); 4.095(0.6); 3.987(1.7);3.882(16.0); 3.678(1.1); 3.659(3.5); 3.641(3.5); 3.622(1.1);3.368(22.6); 3.317(71.3); 3.289(0.6); 2.675(0.6); 2.671(0.8);2.666(0.6); 2.506(88.1); 2.502(114.1); 2.497(86.6); 2.333(0.6);2.328(0.7); 2.324(0.5); 1.236(0.6); 1.192(3.8); 1.174(8.3); 1.163(1.3);1.155(3.7); 0.000(2.2) 2.44 2.43 Example 22: ¹H-NMR(400.0 MHz, d₆-DMSO):= 11.621(2.7); 9.296(4.1); 8.527(2.1); 8.505(4.7); 8.469(4.1);8.446(1.9); 8.314(0.6); 8.302(4.3); 5.754 (11.5); 3.906(0.3);3.884(16.0); 3.649(1.0); 3.631(3.3); 3.612(3.4); 3.594(1.0);3.317(132.9); 2.675(1.1); 2.670(1.5); 2.666(1.1); 2.523(4.1);2.510(83.5); 2.506(168.8); 2.501(224.3); 2.497(167.2); 2.493(85.3);2.332(1.0); 2.328(1.4); 2.324(1.1); 2.053(0.9); 2.037(1.2); 2.022(1.0);1.235 (0.5); 1.183(3.7); 1.165(8.3); 1.146(3.6); 0.911(8.1); 0.896(5.7);0.146(0.4); 0.008(3.0); 0.000(90.5); −0.008(4.1); −0.150(0.4) 2.22 2.34Example 24: ¹H-NMR(400.0 MHz, d₆-DMSO): = 12.166(1.9); 9.302(4.2);8.603(2.1); 8.581(3.3); 8.507(3.0); 8.485(2.0); 8.311(4.7); 6.571(0.9);6.437 (2.1); 6.304(1.0); 4.038(0.3); 4.020(0.4); 3.901(16.0);3.709(1.0); 3.691(3.3); 3.672(3.4); 3.654 (1.0); 3.317(111.8);2.675(0.7); 2.670(1.0); 2.666(0.8); 2.523(2.4); 2.506(126.6);2.501(165.7); 2.497(120.3); 2.333(0.7); 2.328(1.0); 2.323(0.7);1.988(1.5); 1.398(0.8); 1.202(3.6); 1.193(0.9); 1.183(8.2); 1.175(1.3);1.165(3.6); 1.158(0.6); 0.937(0.5); 0.000(55.9); −0.008(2.2) 2.44 2.47Example 25: ¹H-NMR(400.0 MHz, d₆-DMSO): = 9.309(2.3); 8.805(1.7);8.784(1.8); 8.365(1.9); 8.344(1.8); 8.329(2.5); 4.038(0.5); 4.020(0.5);3.933 (0.6); 3.914(2.1); 3.896(10.3); 3.878(0.7); 3.739(16.0);3.689(0.3); 3.317(76.1); 2.675(0.5); 2.670 (0.6); 2.506(84.8);2.501(106.0); 2.497(77.1); 2.328(0.7); 2.323(0.5); 1.988(2.0);1.398(0.7); 1.261(2.1); 1.243(4.5); 1.224(2.0); 1.193(0.5); 1.175(1.0);1.157(0.5); 0.000(23.4) 0.85 1.92 Example 26: ¹H-NMR(400.0 MHz,d₆-DMSO): = 11.715(1.1); 9.288(5.0); 9.264(0.3); 8.418(3.1); 8.396(3.3);8.313(0.5); 8.304(0.4); 8.290(5.3); 7.858 (0.5); 7.795(0.5); 7.790(0.3);7.354(3.1); 7.332(3.1); 5.753(8.5); 4.030(1.2); 3.924(16.0); 3.903(1.2); 3.824(0.5); 3.815(1.5); 3.771(1.1); 3.753(3.5); 3.734(3.5);3.716(1.2); 3.338(19.8); 3.323 (127.2); 3.296(2.4); 3.186(0.5);2.670(1.3); 2.505(164.3); 2.501(213.6); 2.497(163.7); 2.328(1.3);2.291(0.8); 1.234(1.1); 1.216(3.8); 1.198(8.3); 1.179(3.9); 1.166(0.5);0.000(0.9) 2.62 2.73 Example 27: ¹H-NMR(601.6 MHz, CD3CN): = 9.045(2.5);8.786(0.6); 8.328(2.0); 8.313(2.2); 8.130(2.7); 8.129(2.7); 7.978(2.1);7.963(2.0); 3.961 (16.0); 2.935(1.2); 2.922(3.7); 2.910(3.7);2.898(1.2); 2.454(1.2); 2.441(3.7); 2.429(3.8); 2.416 (1.2); 2.129(4.4);1.963(2.9); 1.955(1.1); 1.951(1.3); 1.947(7.1); 1.943 (12.0);1.939(17.0); 1.935 (11.9); 1.931(6.1); 1.212(4.0); 1.200(8.3);1.188(3.9); 1.168(4.0); 1.155(8.2); 1.143(3.9); 0.005 (0.6);0.000(16.0); −0.006(0.5) 2.75 2.81 Example 28: ¹H-NMR(400.0 MHz,d₆-DMSO): = 9.292(3.9); 8.293(4.1); 8.280(3.1); 8.258(3.4); 7.859(3.4);7.838(3.1); 5.754(6.7); 3.903(15.8); 3.751 (1.0); 3.732(3.4);3.714(3.4); 3.695(1.0); 3.328(12.7); 2.601(16.0); 2.525(0.6);2.511(14.8); 2.507 (29.4); 2.503(38.5); 2.498(28.3); 1.208(3.6);1.190(7.9); 1.171(3.5); 0.008(0.5); 0.000(14.0); −0.008(0.6) 3.53 3.62Example 29: ¹H-NMR(400.0 MHz, d₆-DMSO): = 9.287(3.9); 8.313(2.4);8.294(4.2); 8.257(3.1); 8.235(3.4); 7.832(0.3); 7.811(0.3); 7.800(3.3);7.779 (3.1); 5.753(0.6); 4.027(0.5); 4.010(1.1); 3.993(1.5); 3.976(1.1);3.959(0.4); 3.898(16.0); 3.726 (1.0); 3.708(3.1); 3.689(3.3);3.671(1.1); 3.361(1.1); 3.319(609.0); 3.317(609.5); 3.210(0.4); 3.192(0.4); 2.989(0.3); 2.674(4.6); 2.670(6.4); 2.666(4.7); 2.523(18.1);2.510(391.4); 2.506(789.6); 2.501(1038.8); 2.497(748.5); 2.492(361.9);2.458(1.0); 2.454(0.7); 2.449(0.6); 2.395(0.4); 2.332 (4.4); 2.328(6.3);2.323(4.7); 1.371(15.1); 1.354(15.0); 1.321(0.4); 1.302(0.8);1.285(0.4); 1.235 (0.4); 1.203(3.7); 1.184(7.9); 1.166(3.5); 0.974(0.7);0.957(0.4); 0.146(0.9); 0.008(7.7); 0.000(215.6); −0.008(7.9);−0.150(1.0) 3.72 3.81 Example 30: ¹H-NMR(400.0 MHz, d₆-DMSO): =9.292(4.1); 8.303(4.4); 8.283(3.3); 8.261(3.7); 7.878(3.6); 7.857(3.4);7.385(1.8); 7.381(2.3); 7.364 (3.2); 7.362(3.2); 7.309(0.9); 7.303(1.2);7.299(0.6); 7.287(3.7); 7.268(3.2); 7.262(2.4); 7.259 (1.3); 7.253(0.6);7.245(1.3); 7.228(0.4); 5.754(1.9); 4.491(8.1); 3.809(16.0); 3.722(1.0);3.704(3.4); 3.685(3.4); 3.667(1.0); 3.318(57.9); 2.675(0.4); 2.671(0.6);2.666(0.4); 2.524(1.5); 2.510(32.7); 2.506(65.0); 2.502(86.3);2.497(64.0); 2.493(32.2); 2.333(0.4); 2.328(0.5); 2.324(0.4); 1.197(3.6); 1.179(8.1); 1.170(1.0); 1.160(3.6); 0.000(4.0) 1.96 2.01 Example31: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.362(3.9); 8.978(1.0); 8.966(1.0);8.954(0.4); 8.727(3.2); 8.706(3.9); 8.503(3.8); 8.483(3.3); 8.328 (4.2);5.754(2.3); 3.931(16.0); 3.872(1.0); 3.844(1.0); 3.826(3.4); 3.807(3.5);3.789(1.0); 3.319 (32.9); 3.117(0.9); 2.891(0.8); 2.844(7.2);2.832(7.2); 2.732(0.6); 2.671(0.4); 2.541(3.4); 2.524 (0.9);2.511(21.8); 2.506(44.8); 2.502(59.4); 2.497(43.0); 2.493(20.7);2.328(0.4); 2.102(0.4); 1.224 (3.7); 1.206(8.2); 1.187(3.6); 1.176(0.3);1.158(0.5); 0.146(0.4); 0.008(3.1); 0.000(87.0); −0.009 (3.0);−0.150(0.4) 2.22 2.29 Example 32: ¹H-NMR(400.0 MHz, d₆-DMSO): □ =9.360(4.4); 9.051(0.7); 9.037(1.4); 9.022(0.7); 8.725(3.0); 8.704(3.6);8.506(3.6); 8.486(3.1); 8.327 (4.7); 5.753(1.9); 3.928(16.0);3.837(1.1); 3.818(3.5); 3.800(3.6); 3.781(1.1); 3.373(0.6); 3.356 (2.1);3.339(3.2); 3.320(72.2); 2.671(0.4); 2.541(2.9); 2.506(45.8);2.502(59.8); 2.497(45.5); 2.329 (0.4); 1.221(3.7); 1.202(8.2);1.184(3.7); 1.134(4.0); 1.116(8.5); 1.098(3.9); 0.000(65.2) 2.27 2.34Example 33: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.343(4.4); 8.931(1.6);8.919(1.6); 8.719(4.6); 8.706(0.4); 8.698(5.7); 8.496(5.2); 8.487(0.3);8.475 (4.5); 8.326(0.3); 8.317(5.2); 8.308(8.0); 5.750(2.3); 3.926(0.8);3.899(16.0); 3.828(1.0); 3.810 (3.1); 3.791(3.2); 3.773(1.0);3.375(106.8); 3.370(117.3); 3.365(96.6); 3.357(111.1); 3.352(103.8);2.957(0.5); 2.948(0.6); 2.938(1.0); 2.928(0.9); 2.922(0.7); 2.918(0.5);2.910(0.5); 2.673(0.4); 2.543(4.0); 2.527(1.0); 2.522(1.5); 2.513(24.4);2.509(52.2); 2.504(70.6); 2.500(50.9); 2.495(24.0); 2.331(0.4);1.215(4.3); 1.197(9.8); 1.178(4.2); 1.116(0.5); 0.742(0.7); 0.722(2.2);0.712(2.2); 0.709(1.7); 0.705(1.8); 0.703(2.2); 0.695(1.8); 0.682(1.7);0.670(3.4); 0.663(2.1); 0.642(0.4); 0.008 (1.8); 0.000(56.8);−0.009(1.8) 2.76 2.80 Example 34: ¹H-NMR(400.0 MHz, d₆-DMSO): □ =10.989(0.7); 10.977(0.7); 9.359(3.7); 8.895(3.3); 8.874(4.2);8.713(4.1); 8.691(3.4); 8.330(3.9); 8.329(4.0); 8.313(0.4); 3.923(16.0);3.823(1.0); 3.804(3.4); 3.786(3.6); 3.773(1.4); 3.767(1.2); 3.751 (0.4);3.329(41.3); 3.221(7.1); 3.209(7.1); 2.679(0.3); 2.675(0.7); 2.670(1.0);2.666(0.7); 2.661 (0.3); 2.524(2.2); 2.519(3.3); 2.510(57.4);2.506(123.4); 2.501 (167.3); 2.497(119.6); 2.492(56.2); 2.333(0.7);2.328(1.0); 2.323(0.7); 2.319(0.3); 2.086(15.2); 1.223(3.6); 1.204(8.2);1.186(3.5); 0.850(0.4); 0.832(0.5); 0.008(0.5); 0.000(18.5); −0.009(0.6)3.14 3.17 Example 35: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 10.967(1.0);9.355(3.8); 8.870(3.2); 8.849(4.1); 8.706(4.0); 8.685(3.3); 8.329(4.2);8.312(4.0); 3.988 (0.4); 3.923(16.0); 3.831(0.8); 3.824(1.3);3.813(2.0); 3.806(3.9); 3.797(2.5); 3.787(4.0); 3.781 (2.1); 3.769(1.4);3.568(0.4); 3.486(0.4); 3.446(0.7); 3.421(0.8); 3.320(1076.7);3.237(0.5); 3.220 (0.5); 2.942(0.5); 2.675(7.6); 2.670(10.6);2.666(8.0); 2.620(0.5); 2.593(0.6); 2.570(0.9); 2.523 (25.4);2.519(39.7); 2.510(621.7); 2.506(1328.0); 2.501(1803.9); 2.497(1319.3);2.492(643.5); 2.376(0.4); 2.332(7.7); 2.328(10.7); 2.323(8.1);2.153(0.5); 1.231(4.0); 1.221(4.0); 1.213(8.7); 1.202(8.3); 1.195(4.3);1.184(3.5); 1.044(1.7); 1.029(1.6); 0.146(0.4); 0.008(2.9); 0.000(98.7);−0.008 (4.2); −0.150(0.6); −3.075(0.4) 3.14 3.17 Example 36:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 15.381(0.4); 12.894(0.4); 10.721(0.9);10.710(0.7); 9.355(0.5); 9.334(3.9); 8.799(1.1); 8.778(1.4); 8.706(0.4);8.684(2.8); 8.663(1.8); 8.316(4.5); 8.313(4.8); 7.092(0.4); 6.585(0.4);5.854(0.4); 3.949 (0.4); 3.932(0.4); 3.924(1.3); 3.899(16.0);3.872(0.4); 3.825(1.2); 3.807(3.6); 3.788(3.6); 3.770 (1.2); 3.750(0.4);3.734(0.5); 3.717(0.5); 3.714(0.4); 3.671(0.4); 3.655(0.4); 3.639(0.4);3.628 (0.4); 3.599(0.5); 3.594(0.5); 3.575(0.7); 3.563(0.7); 3.539(1.0);3.520(1.1); 3.488(0.6); 3.465(0.9); 3.450(0.9); 3.440(1.0); 3.374(3.1);3.323(1222.9); 3.320(1042.7); 3.256(0.5); 3.233(0.4); 2.942 (1.2);2.675(8.0); 2.670(11.5); 2.666(8.5); 2.661(4.3); 2.627(0.4); 2.604(0.4);2.581(0.7); 2.578(0.7); 2.524(26.8); 2.519(42.0); 2.510(664.6);2.506(1423.0); 2.501(1930.0); 2.497(1406.8); 2.492 (681.2); 2.419(0.8);2.401(0.8); 2.391(0.6); 2.370(0.4); 2.366(0.5); 2.337(3.7); 2.332(8.0);2.328 (11.5); 2.324(8.4); 2.281(0.4); 2.266(0.5); 2.155(1.4);2.142(0.4); 2.085(0.4); 2.073(1.0); 1.642(0.4); 1.216(3.8); 1.197(8.4);1.179(3.7); 1.116(0.5); 1.099(0.4); 1.045(0.4); 1.030(0.5); 0.909(2.5);0.890(4.6); 0.146(0.6); 0.008(3.0); 0.000(102.0); −0.008(4.2);−0.149(0.6); −2.987(0.4); −3.401 (0.4) 2.02 2.03 Example 37:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.304(3.6); 8.830(3.6); 8.809(4.0);8.392(3.9); 8.371(3.7); 8.317(3.8); 8.315(4.0); 8.146(2.2); 3.897(16.0); 3.871(0.8); 3.854(1.7); 3.835(1.9); 3.833(2.0); 3.814(1.8);3.797(0.7); 3.779(0.4); 3.331 (5.1); 3.313(4.0); 3.297(2.9); 3.278(2.1);3.260(0.9); 3.054(0.3); 3.036(1.1); 3.017(1.3); 3.001(1.1); 2.983(0.9);2.525(0.5); 2.520(0.8); 2.512(13.9); 2.507(30.0); 2.503(40.8);2.498(29.8); 2.494 (14.6); 2.086(6.3); 1.239(3.5); 1.221(8.0);1.202(3.5); 1.134(3.7); 1.116(8.3); 1.097(3.6); 0.000(2.8) 2.03 2.05Example 38: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.241(7.9); 8.313(0.5);8.242(8.2); 7.955(1.4); 7.915(0.8); 6.808(3.5); 6.785(3.4); 5.754(3.0);3.859 (16.0); 3.544(1.3); 3.526(3.9); 3.507(3.9); 3.489(1.3);3.318(133.2); 2.851(11.1); 2.839(11.5); 2.675(0.8); 2.671(1.1);2.666(0.9); 2.524(3.6); 2.510(58.4); 2.506(123.6); 2.501(174.1);2.497(134.5); 2.493(68.8); 2.337(0.3); 2.333(0.7); 2.328(1.0);2.324(0.8); 1.162(6.4); 1.144(14.5); 1.125 (6.2); 0.008(1.1);0.000(36.8); −0.008(1.7) 2.66 2.66 Example 39: ¹H-NMR(600.1 MHz,d₆-DMSO): □ = 9.328(3.1); 8.693(3.6); 8.679(3.9); 8.357(3.4);8.355(3.3); 8.063(3.7); 8.049(3.8); 7.305(0.5); 7.303 (0.7); 7.294(3.8);7.292(1.9); 7.290(1.7); 7.283(2.4); 7.277(0.5); 7.274(0.7); 7.268(0.5);7.078 (1.9); 7.075(2.2); 7.065(1.7); 7.062(1.9); 5.756(14.8);4.575(1.7); 4.552(1.9); 4.278(2.1); 4.256(1.8); 3.909(16.0); 3.846(0.5);3.833(0.8); 3.822(1.4); 3.810(1.5); 3.798(1.5); 3.786(1.5); 3.775(0.8);3.762(0.5); 3.320(133.6); 2.617(0.3); 2.613(0.5); 2.610(0.3);2.541(2.9); 2.523(0.8); 2.519(1.0); 2.516(1.0); 2.508(22.7);2.505(50.4); 2.501(70.3); 2.498(50.6); 2.495(23.6); 2.385(0.4);1.352(0.5); 1.235(0.6); 1.210(0.4); 1.202(3.3); 1.197(1.0); 1.189(7.5);1.177(3.3); 0.000(1.5) 3.24 3.33 Example 40: ¹H-NMR(400.0 MHz, d₆-DMSO):□ = 9.280(3.8); 8.398(3.1); 8.377(3.4); 8.279(4.1); 7.833(3.2);7.812(2.9); 6.820(2.1); 6.781(3.1); 6.632 (1.5); 6.608(1.5); 6.594(1.0);6.569(1.0); 5.754(4.6); 3.888(0.5); 3.859(16.0); 3.722(1.0); 3.704(3.3); 3.686(3.3); 3.667(1.0); 3.318(43.7); 2.671(0.4); 2.524(0.9);2.511(23.5); 2.506(50.0); 2.502 (67.8); 2.497(48.8); 2.493(23.1);2.329(0.4); 1.761(0.4); 1.750(0.6); 1.738(0.6); 1.726(0.6); 1.716 (0.4);1.195(3.5); 1.176(7.9); 1.158(3.4); 0.956(0.5); 0.946(1.7); 0.940(1.9);0.926(1.7); 0.920 (1.8); 0.910(0.6); 0.689(0.7); 0.679(2.1); 0.673(2.0);0.668(2.0); 0.662(2.1); 0.652(0.5); 0.146(0.4); 0.008(3.4); 0.000(97.3);−0.009(3.3); −0.150(0.4) 1.79 1.78 Example 41: ¹H-NMR(600.1 MHz,d₆-DMSO): □ = 9.321(3.9); 8.855(3.1); 8.841(3.4); 8.547(3.4);8.533(3.2); 8.335(4.2); 8.244(0.9); 8.241(0.4); 8.232 (0.3); 8.229(0.9);7.901(1.0); 7.890(0.4); 7.887(0.9); 5.756(8.0); 3.940(16.0); 3.911(1.2);3.899 (3.7); 3.886(3.7); 3.874(1.2); 3.510(0.4); 3.496(0.5); 3.484(0.9);3.472(1.3); 3.460(2.0); 3.448(2.3); 3.436(2.3); 3.423(2.0); 3.412(1.2);3.399(0.8); 3.387(0.4); 2.614(0.3); 2.541(O.7); 2.523(0.5); 2.520(0.6);2.517(0.7); 2.505(34.7); 2.502(47.3); 2.499(36.2); 2.386(0.3);1.352(0.6); 1.259(0.5); 1.248(4.0); 1.235(9.1); 1.223(4.0); 1.202(4.2);1.190(8.8); 1.178(4.2); 0.000(6.4) 3.64 3.68 Example 42: ¹H-NMR(600.1MHz, d₆-DMSO): □ = 9.262(1.7); 9.255(3.2); 8.455(0.7); 8.440(0.8);8.319(3.6); 8.305(3.9); 8.291(1.7); 8.290(1.7); 8.280 (3.5); 8.279(3.4);8.265(0.9); 8.251(0.8); 7.735(1.8); 7.732(2.3); 7.729(1.0); 7.727(1.3);7.724 (1.7); 7.719(2.8); 7.585(0.5); 7.582(0.9); 7.581(0.8); 7.577(4.4);7.574(4.2); 7.569(1.7); 7.568(1.6); 7.565(2.3); 7.559(0.5); 7.557(0.7);7.434(3.5); 7.419(3.7); 5.756(5.3); 3.815(0.8); 3.785(16.0); 3.775(7.9);3.742(1.1); 3.729(3.3); 3.722(1.2); 3.717(3.4); 3.709(1.1); 3.705(1.1);3.697(0.4); 3.338 (0.5); 3.322(754.8); 2.619(0.5); 2.617(1.1);2.613(1.5); 2.610(1.1); 2.607(0.5); 2.541(0.5); 2.522 (2.7); 2.519(3.3);2.516(3.1); 2.508(76.3); 2.504(169.4); 2.501 (236.4); 2.498(170.4);2.495(79.6); 2.391(0.5); 2.388(1.1); 2.385(1.5); 2.382(1.1); 2.379(0.5);1.235(0.4); 1.185(3.4); 1.173(7.7); 1.161(3.6); 1.158(2.3); 1.145(4.0);1.133(1.7); 0.000(3.3) 1.75 1.75 Example 43: ¹H-NMR(400.0 MHz, d₆-DMSO):□ = 9.333(4.4); 9.227(0.8); 8.901(3.3); 8.880(3.7); 8.576(3.8);8.555(3.5); 8.338(4.7); 8.314(0.9); 8.238 (0.9); 7.954(1.3); 5.754(6.0);4.325(0.6); 3.977(16.0); 3.944(0.9); 3.926(1.9); 3.915(2.0); 3.908(2.0); 3.897(2.4); 3.873(3.4); 3.862(0.5); 3.749(0.5); 3.550(0.7);3.532(0.7); 3.513(0.4); 3.343(131.0); 3.291(17.6); 3.210(0.5);2.946(0.5); 2.675(1.9); 2.671(2.5); 2.666(1.9); 2.592(0.4); 2.506(292.8); 2.501(404.5); 2.497(314.3); 2.332(1.7); 2.328(2.4); 2.324(1.8);1.261(3.7); 1.243(8.0); 1.225 (3.7); 1.169(0.8); 1.150(1.6); 1.141(0.4);1.132(0.7); 0.008(2.7); 0.000(70.8); −0.149(0.3) 1.81 1.81 Example 44:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.304(3.6); 8.840(3.5); 8.819(3.9);8.441(3.9); 8.420(3.6); 8.317(3.8); 8.316(3.8); 5.754(6.1); 3.913(15.6); 3.904(0.8); 3.886(0.7); 3.869(1.6); 3.850(1.6); 3.845(1.6);3.827(1.6); 3.809(0.7); 3.791 (0.4); 3.317(37.6); 2.947(16.0);2.671(0.4); 2.524(1.0); 2.520(1.4); 2.511(21.6); 2.506(46.0); 2.502(64.6); 2.497(47.9); 2.493(22.6); 2.329(0.4); 1.246(3.3); 1.228(7.5);1.209(3.2); 0.008(0.4); 0.000 (13.9); −0.009(0.4) 2.08 2.08 Example 45:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.330(4.6); 8.902(3.2); 8.882(3.6);8.566(3.7); 8.545(3.3); 8.347(4.9); 8.313(0.4); 5.753(6.3); 3.966(16.0); 3.947(1.1); 3.928(3.6); 3.910(3.7); 3.891(1.1); 3.441(17.8);3.316(79.8); 2.670(1.1); 2.505 (129.2); 2.501(178.4); 2.497(144.2);2.328(1.0); 1.264(3.8); 1.245(8.1); 1.227(3.8); 0.000(26.6) 1.68 1.78Example 46: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.349(2.8); 9.240(0.4);8.723(2.2); 8.702(2.7); 8.505(2.6); 8.484(2.3); 8.372(1.1); 8.326(3.0);8.004 (1.0); 4.254(0.3); 4.074(1.8); 3.941(10.7); 3.901(0.5);3.866(0.7); 3.848(2.2); 3.829(2.3); 3.811 (0.7); 3.338(82.0);2.675(0.5); 2.670(0.6); 2.666(0.5); 2.599(0.4); 2.523(1.5); 2.510(36.5);2.506 (76.7); 2.501(107.5); 2.497(81.7); 2.493(40.2); 2.333(0.4);2.328(0.6); 2.323(0.5); 2.086(16.0); 1.230(2.6); 1.212(5.5); 1.193(2.4);0.008(1.3); 0.000(36.3); −0.008(1.4) 2.08 2.15 Example 47: ¹H-NMR(400.0MHz, d₆-DMSO): □ = 9.341(4.3); 8.835(3.3); 8.814(3.8); 8.438(3.8);8.418(3.5); 8.340(4.5); 8.156(1.8); 5.754(4.2); 3.946 (16.0);3.906(1.1); 3.888(3.6); 3.870(3.6); 3.851(1.1); 3.320(73.5); 2.671(0.4);2.613(13.0); 2.510 (23.0); 2.506(46.6); 2.502(64.2); 2.497(49.8);2.328(0.4); 1.254(3.6); 1.235(8.1); 1.217(3.6) 2.30 2.36 Example 48:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.350(4.3); 8.836(3.4); 8.815(3.8);8.448(3.8); 8.428(3.5); 8.349(4.6); 8.321(0.3); 8.281(1.4); 5.762 (5.4);3.945(16.0); 3.901(1.0); 3.882(3.5); 3.864(3.6); 3.845(1.1);3.327(142.0); 3.028(1.3); 3.016 (1.3); 2.684(0.5); 2.679(0.7);2.675(0.5); 2.514(81.0); 2.510(111.1); 2.505(83.9); 2.341(0.5);2.337(0.7); 2.332(0.5); 1.255(3.7); 1.237(8.1); 1.218(3.6); 1.034(4.4);1.016(9.2); 0.998(4.3) 2.49 2.56 Example 49: ¹H-NMR(400.0 MHz, d₆-DMSO):□ = 9.350(4.5); 8.833(3.3); 8.812(3.8); 8.456(3.8); 8.436(3.5);8.351(4.8); 8.321(0.4); 8.288(1.2); 5.761 (2.2); 3.944(0.6);3.932(16.0); 3.863(1.1); 3.845(3.5); 3.826(3.6); 3.808(1.1); 3.534(0.6);3.519 (0.6); 3.445(0.3); 3.327(111.7); 2.683(0.5); 2.678(0.7);2.674(0.5); 2.532(1.6); 2.514(78.6); 2.509 (108.3); 2.505(82.7);2.340(0.5); 2.336(0.6); 2.332(0.5); 1.241(3.8); 1.222(8.1); 1.204(3.6);1.024 (14.8); 1.008(14.7) 2.47 2.54 Example 50: ¹H-NMR(400.0 MHz,d₆-DMSO): □ = 9.312(2.0); 8.848(1.5); 8.827(1.6); 8.439(1.6);8.418(1.5); 8.342(2.1); 5.761(1.7); 3.969(7.2); 3.907 (0.5); 3.889(1.6);3.870(1.6); 3.852(0.5); 3.327(29.3); 2.885(16.0); 2.514(20.6);2.510(28.2); 2.505 (21.7); 1.262(1.7); 1.244(3.6); 1.225(1.6) 3.36 3.37Example 51: ¹H-NMR(601.6 MHz, d₆-DMSO): □ = 9.284(3.3); 8.345(3.5);8.330(3.7); 8.288(3.6); 8.286(3.5); 7.322(3.6); 7.307(3.7); 5.756(5.7);4.423 (1.5); 4.336(2.3); 4.325(5.1); 4.314(2.4); 3.905(16.0);3.707(0.9); 3.695(3.2); 3.682(3.3); 3.670 (1.0); 3.326(167.7);2.614(0.3); 2.523(0.6); 2.520(0.7); 2.517(0.7); 2.508(18.0);2.505(37.8); 2.502 (50.9); 2.499(37.5); 2.496(17.7); 2.386(0.3);1.777(1.2); 1.766(2.5); 1.753(2.5); 1.742(1.2); 1.194 (3.4); 1.181(7.8);1.169(3.4); 0.977(4.2); 0.964(8.8); 0.952(4.0); 0.000(4.1) 2.51 2.64Example 52: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 10.974(2.9); 9.290(4.2);8.515(12.7); 8.298(4.5); 4.179(10.4); 4.038(0.6); 4.021(0.6);3.880(16.0); 3.674(1.0); 3.656(3.4); 3.637(3.5); 3.619(1.1); 3.590(1.6);3.572(5.1); 3.555(5.1); 3.537(1.6); 3.325 (92.3); 3.319(72.8);2.676(0.4); 2.671(0.6); 2.667(0.4); 2.524(1.3); 2.511(33.9);2.506(68.6); 2.502(90.7); 2.497(66.9); 2.493(33.4); 2.333(0.4);2.329(0.6); 2.324(0.4); 1.988(2.6); 1.398(0.9); 1.192(4.1); 1.178(6.6);1.173(9.2); 1.161(11.1); 1.155(4.4); 1.143(5.1); 0.008(0.8);0.000(23.1); −0.008(0.9) 2.38 2.51 Example 53: ¹H-NMR(400.0 MHz,d₆-DMSO): □ = 11.408(3.0); 9.292(4.2); 8.538(0.6); 8.516(4.9);8.510(5.0); 8.488(0.6); 8.302(4.4); 4.038(0.7); 4.020 (0.7);3.879(13.8); 3.656(1.0); 3.638(3.1); 3.619(3.2); 3.601(1.0); 3.395(8.6);3.325(79.3); 2.671 (0.4); 2.501(60.1); 2.327(0.4); 2.177(16.0);1.988(2.7); 1.398(3.2); 1.189(3.5); 1.171(7.3); 1.152 (3.3);0.000(11.0); −0.001(10.3) 2.12 2.08 Example 54: ¹H-NMR(400.0 MHz,d₆-DMSO): □ = 11.839(2.8); 9.310(3.8); 9.160(2.4); 9.156(2.4);8.795(1.8); 8.791(1.9); 8.783(1.9); 8.779(1.9); 8.684 (2.7); 8.662(4.4);8.591(3.6); 8.568(2.4); 8.387(1.0); 8.382(1.3); 8.377(1.0); 8.367(1.1);8.362 (1.4); 8.357(1.0); 8.313(4.2); 7.589(1.2); 7.576(1.2); 7.569(1.2);7.557(1.1); 4.038(0.4); 4.021(0.3); 3.922(16.0); 3.711(0.9); 3.692(3.2);3.674(3.2); 3.656(1.0); 3.386(0.4); 3.326(457.7); 3.302 (1.3);3.285(0.6); 3.185(0.5); 2.676(0.9); 2.671(1.2); 2.666(0.9); 2.524(3.5);2.511(73.1); 2.506(148.3); 2.502(194.7); 2.497(140.9); 2.493(67.9);2.465(0.4); 2.455(0.3); 2.333(0.8); 2.329(1.2); 2.324 (0.8); 1.988(1.4);1.216(3.6); 1.198(8.1); 1.180(3.4); 1.175(1.4); 1.157(0.4); 0.008(0.4);0.000 (11.7) 1.39 Example 55: ¹H-NMR(400.0 MHz, d₆-DMSO): □ =9.243(8.0); 8.974(2.9); 8.310(0.3); 8.244(7.4); 7.993(1.3); 7.973(1.4);7.058(0.4); 7.042(0.4); 5.751 (1.8); 4.566(2.1); 4.363(0.8); 4.039(0.4);4.021(0.4); 3.844(13.7); 3.522(1.5); 3.503(4.2); 3.485 (4.3);3.467(1.6); 3.337(243.9); 3.333(189.2); 3.331(188.2); 2.672(0.7);2.507(92.9); 2.503(117.9); 2.498(88.3); 2.329(0.7); 1.988(1.5);1.235(0.4); 1.193(0.5); 1.175(1.0); 1.159(7.6); 1.141(16.0); 1.122(7.2);0.008(0.8); 0.000(20.0) 2.35 2.37 Example 56: ¹H-NMR(400.0 MHz,d₆-DMSO): □ = 9.236(4.9); 8.239(4.2); 8.002(0.7); 7.991(1.2);7.978(0.7); 7.914(0.6); 7.892(0.6); 6.799(3.8); 6.777 (3.7); 4.057(0.8);4.039(2.5); 4.021(2.5); 4.003(0.8); 3.854(16.0); 3.540(0.9); 3.522(2.8);3.503 (2.9); 3.485(1.0); 3.358(182.8); 3.348(127.9); 3.319(2.6);3.302(1.7); 3.284(0.7); 2.673(0.4); 2.527 (1.0); 2.522(1.5);2.513(26.4); 2.509(56.2); 2.504(75.4); 2.500(53.6); 2.495(25.1);2.335(0.3); 2.331(0.4); 1.989(11.2); 1.194(2.8); 1.176(5.7); 1.164(5.2);1.158(5.5); 1.146(11.4); 1.127(5.4); 0.000(0.9) 1.81 Example 57:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 11.520(1.4); 11.473(1.5); 9.297(4.1);8.545(0.8); 8.541(0.7); 8.523(3.0); 8.519(3.1); 8.507(4.0); 8.485(1.0);8.308(4.3); 3.887(11.5); 3.665(0.6); 3.646(1.8); 3.633(2.0); 3.628(2.1);3.615(1.8); 3.596 (0.5); 3.319(177.5); 3.258(0.5); 3.238(1.1);3.213(0.9); 3.189(0.5); 3.177(0.6); 3.160(0.6); 3.143 (0.4); 3.092(0.6);3.076(0.4); 3.060(0.8); 3.044(0.6); 2.929(0.7); 2.910(0.7); 2.897(0.6);2.878 (0.4); 2.749(0.8); 2.727(0.7); 2.674(0.8); 2.670(1.0);2.588(16.0); 2.505(135.9); 2.501(170.3); 2.497 (126.6); 2.332(0.8);2.328(1.0); 1.301(4.4); 1.284(4.9); 1.187(2.8); 1.169(5.7); 1.150(2.7);0.008 (2.6); 0.000(47.3) 1.20 2.37 Example 58: ¹H-NMR(400.0 MHz,d₆-DMSO): □ = 9.247(3.8); 8.249(3.9); 8.247(4.0); 8.031(3.5);8.009(3.8); 7.159(3.7); 7.137(3.6); 4.038(0.9); 4.020 (0.9);3.869(16.0); 3.658(0.9); 3.640(3.2); 3.621(3.3); 3.603(0.9);3.319(276.0); 2.675(0.8); 2.670 (1.1); 2.666(0.8); 2.661(0.4);2.523(2.9); 2.510(65.8); 2.506(138.8); 2.501(186.8); 2.496(134.0);2.492(63.4); 2.337(0.4); 2.332(0.8); 2.328(1.1); 2.323(0.8); 2.319(0.4);1.988(4.0); 1.192(1.2); 1.185(3.4); 1.174(2.5); 1.167(7.7); 1.157(1.4);1.148(3.3); 0.000(2.6) 0.90 2.08 Example 59: ¹H-NMR(600.1 MHz, d₆-DMSO):□ = 11.621(1.2); 9.290(4.6); 8.413(3.0); 8.398(3.1); 8.291(5.0);7.371(3.0); 7.357(3.0); 4.364(0.4); 3.923 (16.0); 3.904(2.1);3.774(1.1); 3.762(3.6); 3.750(3.6); 3.738(1.2); 3.485(1.1); 3.473(3.5);3.460 (3.6); 3.448(1.2); 3.325(2.6); 3.172(3.2); 2.504(27.5);1.237(4.2); 1.225(8.6); 1.214(6.9); 1.202 (8.3); 1.190(3.9); 0.000(0.8)2.39 2.37 Example 60: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.250(5.1);8.250(5.5); 8.030(3.0); 8.007(3.3); 7.388(2.3); 7.365(2.2); 5.757(2.2);5.248(1.3); 5.233 (1.3); 3.870(16.0); 3.575(1.1); 3.556(3.6);3.538(3.7); 3.519(1.3); 3.322(31.7); 3.296(0.5); 3.235 (15.8);2.550(7.4); 2.536(7.5); 2.503(39.6); 1.236(0.3); 1.172(3.7); 1.154(8.0);1.135(3.7); 0.000 (11.4) 2.02 Example 61: ¹H-NMR(400.0 MHz, d₆-DMSO): □= 11.489(2.8); 9.297(4.4); 8.543(0.9); 8.521(5.6); 8.513(5.2);8.491(0.9); 8.310(4.7); 4.056(0.7); 4.038 (2.1); 4.020(2.2); 4.003(0.7);3.884(16.0); 3.648(1.0); 3.630(3.6); 3.611(3.5); 3.593(2.0); 3.569(0.8); 3.320(269.6); 3.298(2.6); 3.279(0.8); 3.271(1.6); 3.260(0.9);3.008(15.6); 2.675(0.7); 2.670 (1.0); 2.666(0.7); 2.523(2.3);2.506(124.3); 2.501(164.0); 2.497(119.1); 2.333(0.7); 2.328(1.0);2.324(0.7); 1.988(9.0); 1.284(5.8); 1.267(5.7); 1.192(2.6); 1.185(3.8);1.175(5.3); 1.167(8.3); 1.157(2.8); 1.148(3.6); 0.000(8.3) 2.47 2.54Example 62: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 11.301(2.7); 9.315(4.0);8.530(1.6); 8.508(5.1); 8.488(4.5); 8.466(1.5); 8.326(4.2); 8.324(4.3);5.753 (0.6); 3.881(15.9); 3.669(0.9); 3.651(3.3); 3.632(3.3);3.614(1.0); 3.316(68.8); 2.675(0.5); 2.671 (0.6); 2.666(0.5);2.524(1.7); 2.510(34.5); 2.506(71.8); 2.501(96.1); 2.497(69.9);2.492(33.9); 2.333(0.5); 2.328(0.6); 2.324(0.4); 2.285(0.5);2.173(16.0); 1.234(0.5); 1.188(3.6); 1.169(8.2); 1.151(3.6); 0.008(2.1);0.000(62.0); −0.008(2.4) 2.60 Example 63: ¹H-NMR(400.0 MHz, d₆-DMSO): □= 12.689(2.0); 9.304(4.2); 8.602(1.7); 8.580(1.6); 8.312(4.7);4.038(0.8); 4.020(0.8); 3.908(16.0); 3.711(1.0); 3.692(3.4); 3.674(3.5);3.655(1.1); 3.354(108.5); 3.344(170.1); 3.336(128.4); 3.331 (129.7);2.743(5.0); 2.675(0.8); 2.671(1.0); 2.667(0.8); 2.524(2.1);2.506(128.7); 2.502(167.3); 2.498 (123.2); 2.329(0.9); 2.324(0.7);1.988(3.4); 1.398(0.7); 1.236(0.6); 1.205(3.6); 1.187(8.2); 1.175 (2.4);1.168(3.7); 1.157(1.0); 0.008(1.1); 0.000(35.9) 2.49 2.55 Example 64:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.246(2.4); 8.247(2.1); 8.033(1.8);8.010(1.9); 7.021(1.8); 6.998(1.7); 4.039(0.4); 4.021(0.4); 3.870 (8.4);3.580(0.6); 3.562(1.8); 3.544(1.9); 3.525(0.6); 3.362(178.0);3.351(136.0); 3.349(147.2); 3.158(16.0); 2.673(0.4); 2.527(0.8);2.513(21.4); 2.509(45.6); 2.504(61.9); 2.500(45.6); 2.331 (0.4);1.989(1.7); 1.194(0.4); 1.173(2.1); 1.155(4.1); 1.136(1.8); 0.000(0.5)2.78 2.94 Example 65: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 11.399(2.3);9.292(3.3); 8.581(1.9); 8.558(3.4); 8.502(3.0); 8.480(1.8); 8.303(3.5);4.039(0.8); 4.021 (0.8); 3.877(12.5); 3.634(0.7); 3.616(2.4);3.597(2.4); 3.579(0.8); 3.324(48.4); 3.015(0.4); 2.999 (0.6);2.979(0.7); 2.962(0.5); 2.810(0.9); 2.789(0.8); 2.777(1.2); 2.756(1.0);2.713(0.3); 2.698 (0.3); 2.681(0.5); 2.583(0.4); 2.566(0.5); 2.557(1.1);2.550(0.5); 2.542(1.2); 2.524(2.2); 2.510(18.4); 2.506(36.6);2.502(47.9); 2.497(35.8); 2.493(18.5); 2.476(0.6); 2.072(16.0);2.051(4.8); 1.988 (3.3); 1.398(1.0); 1.190(5.9); 1.184(3.9); 1.173(6.4);1.165(6.9); 1.158(1.5); 1.147(2.9); 1.136(2.2); 1.119(2.1); 0.008(0.5);0.000(11.5); −0.008(0.5) 2.58 2.60 Example 66: ¹H-NMR(400.0 MHz,d₆-DMSO): □ = 10.761(3.0); 9.306(3.9); 9.297(4.4); 9.292(4.5);8.761(4.5); 8.756(4.4); 8.659(2.4); 8.637(5.2); 8.601 (4.2); 8.579(2.0);8.311(4.0); 8.309(4.1); 4.056(0.5); 4.038(1.7); 4.021(1.7); 4.003(0.6);3.941 (16.0); 3.755(0.9); 3.737(3.2); 3.718(3.3); 3.700(1.0);3.322(207.0); 2.675(0.4); 2.671(0.6); 2.666 (0.4); 2.524(1.4);2.511(33.6); 2.506(69.9); 2.502(93.1); 2.497(68.1); 2.493(33.4);2.333(0.4); 2.329(0.6); 2.324(0.4); 1.989(7.6); 1.235(0.7); 1.225(3.6);1.207(8.1); 1.193(2.7); 1.188(3.6); 1.175 (4.0); 1.157(2.0); 0.000(6.8)2.14 2.14 Example 67: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.256(4.2);8.267(4.5); 7.948(3.0); 7.926(3.2); 7.418(2.6); 6.772(3.3); 6.749(3.2);3.828(16.0); 3.502 (1.0); 3.484(3.3); 3.465(3.4); 3.447(1.0);3.316(40.1); 2.675(0.4); 2.670(0.5); 2.666(0.4); 2.523 (1.2);2.510(28.4); 2.506(58.8); 2.501(79.0); 2.497(58.7); 2.492(29.6);2.332(0.3); 2.328(0.5); 2.324(0.4); 2.073(1.3); 1.153(3.5); 1.134(8.0);1.116(3.4); 0.146(0.3); 0.008(2.5); 0.000(70.1); −0.008 (2.9);−0.150(0.3) 2.99 2.96 Example 68: ¹H-NMR(400.0 MHz, d₆-DMSO): □ =12.293(0.3); 11.562(3.1); 9.297(4.6); 8.518(1.3); 8.495(5.1);8.481(4.7); 8.459(1.3); 8.305(4.9); 7.360(0.9); 7.346(10.2); 7.340(5.7);7.330(5.4); 7.310(2.6); 7.293(2.0); 7.281(0.9); 7.275(1.3); 7.262 (3.7);7.244(2.1); 3.880(16.0); 3.799(8.9); 3.638(1.0); 3.619(3.4); 3.601(3.5);3.582(1.1); 3.558 (5.0); 3.319(57.2); 2.671(0.6); 2.506(83.4);2.502(107.6); 2.498(81.7); 2.329(0.6); 1.989(0.5); 1.398(1.6);1.174(3.9); 1.156(8.2); 1.137(3.6); 0.008(1.5); 0.000(39.5) 2.10 2.11Example 69: ¹H-NMR(601.6 MHz, d₆-DMSO): □ = 9.285(3.4); 8.483(3.2);8.468(3.7); 8.311(1.0); 8.292(3.7); 8.246(3.3); 8.232(2.9); 6.232(0.3);3.916 (16.0); 3.755(1.0); 3.742(3.4); 3.730(3.3); 3.718(1.1);3.455(16.6); 3.315(545.9); 2.619(0.6); 2.616 (1.2); 2.613(1.8);2.610(1.4); 2.522(2.8); 2.519(3.3); 2.516(3.2); 2.507(87.5);2.504(193.9); 2.501(272.8); 2.498(200.1); 2.495(95.3); 2.448(0.5);2.446(0.5); 2.385(2.0); 2.382(1.4); 2.350(0.4); 2.342(15.7); 1.215(3.6);1.202(7.9); 1.190(3.6); 0.097(0.4); 0.005(2.2); 0.000(90.8); −0.006(3.9); −0.100(0.5) 1.68 1.63 Example 70: ¹H-NMR(400.0 MHz, d₆-DMSO): □ =11.622(2.6); 9.296(3.7); 8.534(8.8); 8.310(3.9); 4.136(1.9); 4.103(2.5);3.933(2.6); 3.902(11.8); 3.884(14.4); 3.672(0.8); 3.653(2.9);3.635(3.0); 3.616(0.9); 3.395(0.4); 3.322(224.0); 2.710(16.0);2.675(0.5); 2.670(0.6); 2.666(0.5); 2.524(1.3); 2.510(35.5);2.506(75.5); 2.501(102.4); 2.497(75.2); 2.492(37.1); 2.333(0.4);2.328(0.6); 2.324(0.5); 2.176(0.7); 1.235(0.4); 1.190(3.3); 1.172(7.4);1.153(3.2); 0.000(5.3) 2.46 2.44 Example 71: ¹H-NMR(400.0 MHz, d₆-DMSO):□ = 9.277(2.6); 8.630(1.7); 8.607(2.2); 8.454(0.9); 8.431(0.7);8.291(2.8); 4.056(0.4); 4.038(1.2); 4.020 (1.2); 4.003(0.4); 3.852(0.6);3.833(2.1); 3.816(10.1); 3.796(0.7); 3.318(63.7); 2.671(0.4); 2.523(1.1); 2.506(48.3); 2.501(67.7); 2.497(53.7); 2.361(16.0); 2.317(7.8);1.989(5.2); 1.398(2.7); 1.243 (2.1); 1.225(4.7); 1.206(2.1); 1.192(1.4);1.175(2.7); 1.157(1.3); 0.008(0.6); 0.000(17.2) 1.92 1.87 Example 72:¹H-NMR(400.0 MHz, d₆-DMSO): □ = 11.740(2.3); 9.300(5.0); 8.572(1.4);8.551(4.2); 8.530(3.6); 8.508(1.3); 8.315(5.3); 4.487(7.1); 3.887(16.0); 3.824(0.8); 3.677(1.1); 3.659(3.7); 3.641(3.8); 3.622(1.2);3.411(0.3); 3.371(0.5); 3.320 (512.6); 3.288(0.9); 3.206(14.6);2.671(2.4); 2.560(0.4); 2.505(329.6); 2.501(378.9); 2.433(0.4);2.328(2.4); 1.193(3.9); 1.174(8.4); 1.156(3.9); 1.131(0.4); 0.147(0.4);0.004(42.3); 0.001(81.9); 0.000(87.0); −0.026(0.4); −0.148(0.5) 3.373.37 Example 73: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 11.683(3.2);9.310(4.4); 8.669(2.7); 8.647(4.2); 8.572(3.7); 8.549(2.4); 8.313(5.0);8.076(4.6); 8.055 (5.0); 7.951(3.8); 7.946(1.4); 7.929(4.1); 7.625(5.1);7.603(4.5); 7.579(4.1); 7.557(3.5); 4.038 (0.4); 4.021(0.4);3.919(16.0); 3.707(1.0); 3.689(3.4); 3.670(3.4); 3.652(1.1);3.323(131.1); 2.671 (0.9); 2.506(116.8); 2.502(145.0); 2.498(105.3);2.333(0.7); 2.329(0.9); 2.325(0.7); 1.989(1.6); 1.351(0.3); 1.213(3.7);1.195(8.4); 1.176(4.2); 1.158(0.5); 0.008(1.8); 0.000(44.2); −0.008(2.1)1.96 Example 74: ¹H-NMR(400.0 MHz, d₆-DMSO): □ = 9.243(3.9); 8.247(4.2);7.991(3.4); 7.968(3.7); 7.443(1.8); 7.420(1.7); 5.755(1.7); 5.054(5.3);3.855 (16.0); 3.554(0.9); 3.536(3.1); 3.517(3.2); 3.499(1.0);3.320(160.6); 3.293(15.6); 2.675(0.5); 2.670 (0.7); 2.666(0.5);2.524(1.8); 2.519(2.7); 2.510(38.7); 2.506(82.9); 2.501(117.0);2.497(87.9); 2.492(42.1); 2.333(0.5); 2.328(0.7); 2.323(0.5);1.163(3.3); 1.145(7.6); 1.126(3.2); 0.008(1.3); 0.000(42.5); −0.009(1.5)

Use Examples

Phaedon cochleariae-Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha: 1,2, 3, 4, 6, 7, 8, 10, 13, 14, 15, 16, 21, 22, 24, 26, 27, 31, 32, 36,37, 38, 40, 43, 46, 51, 52, 53, 54, 55, 56, 57, 60, 61, 62, 63, 64, 65,66, 67, 68, 69, 70, 72, 74

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha: 9,20

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha: 73

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 100 g/ha: 33

Spodoptera frugiperda-Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Leaf disks of maize (Zea mays) are sprayed with an active compoundpreparation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillars have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:21, 40, 62, 64, 67

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha: 10

Myzus persicae Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha: 3,4, 16, 24, 31, 52, 55, 56, 61, 65, 70, 72

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha: 2,7, 8, 9, 10, 13, 14, 20, 21, 34, 36, 37, 38, 43, 44, 53, 57, 63, 64, 67,69, 74

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha: 59

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha: 60,66

Tetranychus urticae-Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound preparation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:31, 34, 67

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha: 24,33, 56, 58, 62, 74

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 90% at an application rate of 100 g/ha: 60

Meloidogyne incognita-Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active compound solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 100% at an application rate of 20 ppm: 56,65

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 90% at an application rate of 20 ppm: 11,14, 18, 29, 62

Boophilus microplus-Injection Test

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of solvent and the concentrate is dilutedwith solvent to the desired concentration.

1 μl of the active compound solution is injected into the abdomen of 5engorged adult female cattle ticks (Boophilus microplus). The animalsare transferred into dishes and kept in a climate-controlled room.

Efficacy is assessed after 7 days by laying of fertile eggs. Eggs whichare not visibly fertile are stored in a climate-controlled cabinet untilthe larvae hatch after about 42 days. An efficacy of 100% means thatnone of the ticks has laid any fertile eggs; 0% means that all the eggsare fertile.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 80% at an application rate of 20 μg/animal:14, 22

Ctenocephalides felis-Oral Test

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulphoxide. Dilution withcitrated cattle blood gives the desired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active compound preparation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm: 8,14, 22

Lucilia cuprina Test

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive compound preparation of the desired concentration.

After 2 days, the kill in % is determined. 100% means that all thelarvae have been killed; 0% means that no larvae have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm: 8,10, 14 In this test, for example, the following compounds from thepreparation examples show an efficacy of 90% at an application rate of100 ppm: 22

Musca domestica Test

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulphoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activecompound preparation of the desired concentration are populated with 10adult houseflies (Musca domestica).

After 2 days, the kill in % is determined. 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm: 8,22

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 ppm: 10

Myzus persicae Spray Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water. If the addition of ammonium salts or/andpenetrants is required, these are each added in a concentration of 1000ppm to the formulation solution.

Bell pepper plants (Capsicum annuum) severely infested with the greenpeach aphid (Myzus persicae) are treated by spraying with the activecompound preparation in the desired concentration.

After 6 days, the kill in % is determined. 100% means that all of theaphids have been killed; 0% means that none of the aphids have beenkilled.

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 100% at an application rate of 100 ppm:22, 40

Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas

For the coating of the test tubes, 9 mg of active compound are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μl of the solution are distributedhomogeneously on the inner walls and the base of a 25 ml test tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm active compound solution and internal surface 44.7cm², given homogeneous distribution, an area-based dose of 5 μg/cm² isachieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult cat fleas (Ctenocephalides felis), sealed with a perforatedplastic lid and incubated in a horizontal position at room temperatureand ambient humidity. After 48 h, efficacy is determined. To this end,the test tubes are stood upright and the fleas are knocked to the baseof the tube. Fleas which remain motionless at the base or move in anuncoordinated manner are considered to be dead or moribund.

A substance shows good efficacy against Ctenocephalides felis if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the fleas were dead or moribund. 0%efficacy means that no fleas were harmed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 5 μg/cm²(500 g/ha): 22

Anopheles Test (ANPHGB Surface Treatment)

Solvent: acetone+2000 ppm rapeseed oil methyl ester (RME)

To produce an appropriate active compound formulation, the activecompound is dissolved in the solvent (2 mg/ml). The active compoundformulation is pipetted onto a glazed tile and, after it has dried off,adult mosquitoes of the species Anopheles gambiae strain RSPH (homozygotkdr) are placed onto the treated tile. The exposure time is 30 minutes.

24 hours after contact with the treated surface, mortality in % isdetermined. 100% means that all mosquitoes have been killed; 0% meansthat none of the mosquitoes have been killed.

In this test, for example, the following compounds from the preparationexamples show efficacy of 80-100% at an application rate of 100 mg/m²:14

In this test, for example, the following compounds from the preparationexamples show efficacy of 80-100% at an application rate of 20 mg/m²: 14

Anopheles Test (ANPHFU Surface Treatment)

Solvent: acetone+2000 ppm rapeseed oil methyl ester (RME)

To produce an appropriate active compound formulation, the activecompound is dissolved in the solvent (2 mg/ml). The active compoundformulation is pipetted onto a glazed tile and, after it has dried off,adult mosquitoes of the species Anopheles funestus strain FUMOZ-R (Huntet al., Med Vet Entomol. 2005 September; 19(3):271-5) are placed ontothe treated tile. The exposure time is 30 minutes.

24 hours after contact with the treated surface, mortality in % isdetermined. 100% means that all mosquitoes have been killed; 0% meansthat none of the mosquitoes have been killed.

In this test, for example, the following compounds from the preparationexamples show efficacy of 80-100% at an application rate of 100 mg/m²:14

In this test, for example, the following compounds from the preparationexamples show efficacy of 80-100% at an application rate of 20 mg/m²: 14

Aedes Test (AEDSAE Surface Treatment)

Solvent: acetone+2000 ppm rapeseed oil methyl ester (RME)

To produce an appropriate active compound formulation, the activecompound is dissolved in the solvent (2 mg/ml). The active compoundformulation is pipetted onto a glazed tile and, after it has dried off,adult mosquitoes of the species Aedes aegypti strain MONHEIM are placedonto the treated tile. The exposure time is 30 minutes.

24 hours after contact with the treated surface, mortality in % isdetermined. 100% means that all mosquitoes have been killed; 0% meansthat none of the mosquitoes have been killed.

In this test, for example, the following compounds from the preparationexamples show efficacy of 80-100% at an application rate of 100 mg/m²:14

In this test, for example, the following compounds from the preparationexamples show efficacy of 80-100% at an application rate of 20 mg/m²: 14

The invention claimed is:
 1. A compound of formula (I)

wherein A¹ represents nitrogen, A² represents N—R⁵, A⁴ represents C—H,R¹ represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl ortert-butyl, R^(2a) represents hydrogen, R^(2b) represents a groupselected from —C(═O)—R⁸ (Q1), where R⁸ represents methoxy or ethoxy,—C(═O)—NR¹¹R¹² (Q3), where R¹¹ represents hydrogen or methyl and R¹²represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, tert-butyl or cyclopropyl, —C(═S)—NR¹¹R¹² (Q4), where R¹¹represents hydrogen or methyl and R¹² represents methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,—S(O)_(m)—R¹³ (Q5), where m represents 0, 1 or 2 and R¹³ representsmethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,phenyl or benzyl, —S═O(═NH)—R¹³ (Q6), where R¹³ represents methyl,ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,—S(═N—CN)—R¹³ (Q8), where R¹³ represents methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl or tert-butyl, —S(O)₂—NR¹¹R¹² (Q9), whereR¹¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl orcyclopropyl and R¹² represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl, —NR¹¹R¹² (Q10),where R¹¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl orcyclopropyl and R¹² represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl, —NR¹¹—NR¹¹R¹²(Q11), where R¹¹ represents hydrogen, methyl, ethyl, n-propyl,isopropyl, cyclopropyl or COmethyl (acetyl) and R¹² represents hydrogen,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,cyclopropyl or COmethyl (acetyl), —NR¹¹—C(═O)—R⁸ (Q12), where R¹¹represents hydrogen or methyl and R⁸ represents methyl, ethyl, n-propyl,isopropyl (where R⁸ represents methyl, ethyl, n-propyl, or isopropylonly if R¹¹ does not represent hydrogen), trifluoromethyl, CHF₂, CF₂CF₃,CF₂CHF₂, CH₂OCH₃, CH₂SCH₃, CH₂OC₂H₅, CH₂SOCH₃, CH₂SO₂CH₃,CH(CH₃)CH₂SCH₃, CH(CH₃)CH₂SOCH₃, CH(CH₃)CH₂SO₂CH₃, C₂H₄OC₂H₅, C₂H₄SC₂H₅, C₂H₄OC₂H₅, C₂H₄SOC₂H₅, C₂H₄SO₂C₂H₅, CH(CH₃)CH₂SC₂H₅,CH(CH₃)CH₂SOC₂H₅, CH(CH₃)CH₂SO₂C₂H₅, cyclopropyl, cyclopropylmethyl(—CH₂-cyclopropyl), phenyl, benzyl,

NR¹¹—C(═S)—R⁸ (Q13), where R⁸ represents methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl and R¹¹represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl,—NR¹¹—S(O)₂—R¹³ (Q14), where R¹¹ represents hydrogen, methyl, ethyl,n-propyl, isopropyl, methylsulphonyl or cyclopropyl and R¹³ representsmethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,cyclopropyl or trifluoromethyl, and —O—R¹³ (Q17), where R¹³ representstrifluoromethyl-1H-pyrazol-5-yl

with the proviso that if R^(2b) represents Q5, Q6, Q8 or Q9, then nrepresents 2, R³ represents fluoromethyl, difluoromethyl,trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,tetrafluoroethyl or pentafluoroethyl, R⁵ represents methyl, ethyl orisopropyl, and n is 0, 1 or
 2. 2. The compound of formula (I) accordingto claim 1 wherein A¹ represents nitrogen, A² represents N—R⁵, A⁴represents C—H, R¹ represents ethyl, R^(2a) represents hydrogen, R^(2b)represents a group selected from Q1, where R⁸ represents methoxy, Q3,where R¹¹ represents hydrogen and R¹² represents hydrogen, methyl, ethylor cyclopropyl, Q4, where R¹¹ represents hydrogen and R¹² representsmethyl, ethyl or cyclopropyl, Q5, where m represents 0, 1 or 2 and R¹³represents methyl, ethyl, isopropyl, phenyl or benzyl, Q6, where R¹³represents ethyl, Q8, where R¹³ represents methyl, Q9, where R¹¹represents hydrogen or methyl and R¹² represents methyl, ethyl orisopropyl, Q10, where R¹¹ represents hydrogen or methyl and R¹²represents hydrogen, methyl or ethyl, Q11, where R¹¹ representshydrogen, methyl or COmethyl (acetyl) and R¹² represents hydrogen,methyl or COmethyl (acetyl), Q12, where R¹¹ represents hydrogen ormethyl and R⁸ represents methyl (only if R¹¹ does not representhydrogen), trifluoromethyl, CHF₂, CF₂CF₃, CF₂CHF₂, CH₂OCH₃, CH₂SCH₃,CH₂OC₂H₅, CH₂SOCH₃, CH₂SO₂CH₃, CH(CH₃)CH₂SCH₃, CH(CH₃)CH₂SOCH₃,CH(CH₃)CH₂SO₂CH₃, cyclopropyl, cyclopropylmethyl (—CH₂-cyclopropyl),phenyl, benzyl,

Q13, where R⁸ represents methyl and R¹¹ represents hydrogen, Q14, whereR¹¹ represents hydrogen or methylsulphonyl and R¹³ represents methyl,ethyl or trifluoromethyl, and Q17, where R¹³ representstrifluoromethyl-1H-pyrazol-5-yl

with the proviso that if R^(2b) represents Q5, Q6, Q8 or Q9, then nrepresents 2, R³ represents trifluoromethyl or pentafluoroethyl, R⁵represents methyl, and n is 0, 1 or
 2. 3. The compound of formula (I)according to claim 1 wherein A¹ represents nitrogen, A² represents N—R⁵,A⁴ represents C—H, R¹ represents methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl or tert-butyl, R^(2a) represents hydrogen, R^(2b)represents a group selected from the group consisting of

R³ represents fluoromethyl, difluoromethyl, trifluoromethyl,fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl orpentafluoroethyl, R⁵ represents methyl, ethyl or isopropyl, and nrepresents 0 or 2, with the proviso that if R^(2b) represents Q5a-j,Q6a, Q8a, or Q9a-d, then n represents
 2. 4. The compound of formula (I)according to claim 1 wherein A¹ represents nitrogen, A² represents N—R⁵,A⁴ represents C—H, R¹ represents ethyl, R^(2a) represents hydrogen, R³represents trifluoromethyl or pentafluoroethyl, R⁵ represents methyl, nrepresents 0 or 2, and R^(2b) is selected from the group consisting of

with the proviso that if R^(2b) represents Q5a-j, Q6a, Q8a or Q9a-d,then n represents
 2. 5. The compound of formula (I) according to claim 1wherein R¹, R^(2a), R^(2b), R³, A¹, A², A⁴ and n have the meanings givenin the table: R¹ n A⁴ A² A¹ R^(2a) R³ R^(2b) ethyl 2 CH N-methyl N H CF₃

ethyl 2 CH N-methyl N H CF₃

.


6. An agrochemical formulation comprising one or more compounds offormula (I) according to claim 1 and one or more extenders and/orsurfactants.
 7. The agrochemical formulation according to claim 6,additionally comprising a further agrochemically active compound.
 8. Amethod for controlling one or more animal pests, comprising allowing acompound of formula (I) according to claim 1 or an agrochemicalformulation thereof to act on the animal pests and/or a habitat thereof.9. A product comprising one or more compounds of formula (I) accordingto claim 1 or one or more agrochemical formulations thereof forcontrolling animal pests.
 10. The compound of formula (I) according toclaim 1, wherein R^(2b) represents

R³ represents trifluoromethyl, and n is
 2. 11. The compound of formula(I) according to claim 1, wherein R^(2b) represents

R³ represents trifluoromethyl, and n is
 2. 12. The compound of formula(I) according to claim 1, wherein R^(2b) represents

R³ represents trifluoromethyl, and n is
 2. 13. The compound of formula(I) according to claim 1, wherein R^(2b) represents

R³ represents trifluoromethyl, and n is 2.